WO2011061330A2 - Utilisation d'agents rafraîchissants physiologiques et produits contenant de tels agents - Google Patents

Utilisation d'agents rafraîchissants physiologiques et produits contenant de tels agents Download PDF

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Publication number
WO2011061330A2
WO2011061330A2 PCT/EP2010/067936 EP2010067936W WO2011061330A2 WO 2011061330 A2 WO2011061330 A2 WO 2011061330A2 EP 2010067936 W EP2010067936 W EP 2010067936W WO 2011061330 A2 WO2011061330 A2 WO 2011061330A2
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WIPO (PCT)
Prior art keywords
branched
groups
straight
chain
compounds
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PCT/EP2010/067936
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German (de)
English (en)
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WO2011061330A3 (fr
WO2011061330A9 (fr
Inventor
Horst Surburg
Michael Backes
Heiko Oertling
Arnold Machinek
Hubert Loges
Ulrike Simchen
Thomas Subkowski
Claus Bollscheiler
Jenz Wittenberg
Wolfgang Siegel
Original Assignee
Symrise Ag
Basf Se
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Application filed by Symrise Ag, Basf Se filed Critical Symrise Ag
Priority to JP2012539353A priority Critical patent/JP6017310B2/ja
Priority to EP10787717.7A priority patent/EP2501761B1/fr
Priority to CN201911393855.4A priority patent/CN111053775B/zh
Priority to CN201080061894.5A priority patent/CN102844386B/zh
Priority to EP19194016.2A priority patent/EP3663366A3/fr
Priority to ES10787717T priority patent/ES2812550T3/es
Priority to US13/510,454 priority patent/US8927605B2/en
Publication of WO2011061330A2 publication Critical patent/WO2011061330A2/fr
Publication of WO2011061330A3 publication Critical patent/WO2011061330A3/fr
Publication of WO2011061330A9 publication Critical patent/WO2011061330A9/fr
Priority to US15/629,015 priority patent/US10584134B2/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/20—Spiro-condensed systems
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
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    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
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    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
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    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
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    • A23L27/205—Heterocyclic compounds
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    • C07C2601/14—The ring being saturated

Definitions

  • the invention relates to novel modulators of the cold menthol receptor TRPM8, methods for modulating the TRPM8 receptor using these modulators; the use of modulators to induce coldness; and the articles and compositions made using these modulators.
  • the invention relates to an agent comprising at least one selected such modulator for achieving a cooling effect on the skin or mucosa, wherein the cooling effect is longer lasting compared to the known cooling agent Menthan-3-carboxylic acid N-ethylamide (WS3).
  • WS3 Menthan-3-carboxylic acid N-ethylamide
  • the specific aspect of the invention relates to agents comprising such selected TRPM8 receptor modulators, which agents serve specific purposes.
  • the specific aspect of the invention relates to a method for achieving a physiological cooling effect on the skin or mucous membrane, in which the latter means are used.
  • the cold-menthol receptor TRPM8 (also referred to as Cold-Membrane Receptor (CMR) 1) belongs to the family of "Transient Receptor Potential Ion Channels", becomes specific in one expresses specific pores of neurons and forms pores in the cell membrane (in each case 4 units combine to form a tetramer), which selectively allow Ca 2+ ions to pass through.
  • the protein has 6 transmembrane domains and a cytoplasmic C- and N-terminus. By low temperatures (preferably 10-25 ° C), this receptor is stimulated, it comes to a signal transduction, which is interpreted by the nervous system as a feeling of cold.
  • the receptor has been described for the first time as a cold receptor in several publications in 2002 (Peier AM et al., A TRP Channel that senses cold stimuli and menthol. Cell 2002 Mar 8; 108 (5): 705-15; McKemy DD et al in 2002, 716 (6876): 52-8; Zuker CS: Neurobiology: A cool ion Channel Nature 2002 Mar 7; 416 (6876): 27-8)
  • Cooling compounds such as menthol
  • the compound menthol has been shown to act as a natural modulator of the receptor TRPM8 (McKemy DD, Molecular Pain 1, 2005, 16; McKemy DD, Nature 416, 2002, 52-58; Peier AM, Cell 108, 2002; 705-715; Dhaka A., Annu Rev. Neurosci 29, 2006, 135-161).
  • TRPM8 By application of menthol TRPM8 is activated, causing a Ca 2+ influx into the cold-sensitive neurons. The electrical signal generated thereby is finally perceived as a feeling of cold. Excessive menthol concentrations cause irritation and anesthetic effects.
  • the compound may be in chemically pure or enriched form, as a single stereoisomer or in the form of stereoisomeric mixtures.
  • PCT / EP2009 / 061019 the generic disclosure that the compounds described there may be uncharged or in the form of their salts, such as acid addition salt. Specifically disclosed, however, are no such salts.
  • PCT / EP2009 / 061019 has the generic disclosure that, where appropriate, functional groups present in the compounds described there may be replaced by equivalent chemical groups; for example, oxygen groups (such as ether groups) may be replaced by corresponding sulfur groups and vice versa; Keto groups may be replaced by corresponding thionyl groups. Specifically, however, disclosed are no such modifications.
  • the object of the present invention was therefore to identify new substances which lead to a modulation of the TRPM8 receptor, which can be used as alternatives to the previously known modulators.
  • Such compounds should also be particularly useful in cosmetic applications (e.g., hair care, skin care, oral care), nutrition (feed / food), textile, OTC products (e.g., branded ointment), pharmaceuticals (e.g., tumor treatment, bladder dysfunction), or packaging.
  • FIG. 1 shows (a) the mRNA sequence (SEQ ID NO: 1) or (b) the amino acid sequence derived therefrom (SEQ ID NO: 2) of the hTRPM8 receptor according to sequence database entry NM 024080.
  • FIG. 2 shows the vector map of the hTRPM8-encoding plasmid plnd_M8, which was used for transfecting the HEK293 cells. Detailed description of the invention:
  • TRPM8 transient receptor potential cation Channel subfamily M member 8.
  • TRPP8 LTRPC6, CMR1, MGC2849, transient receptor potential cation Channel subfamily M member 8.
  • onalen modifications of the receptor in particular splice variants, isoforms, such as TRPM8 CRA_a, TRPM8 CRA_b and all analog receptors from different organisms, such as human, mouse, rat.
  • the nucleotide or amino acid sequences of the various receptors are known per se and stored in sequence databases. For example, the sequence information for hTRPM8 is entered under the number NM_024080.
  • a “modulator” within the meaning of the invention is a compound which can act as an agonist and / or antagonist of the TRPM8 receptor in vivo and / or in vitro, in particular in vivo Suitable modulators may be either only as antagonist or agonist, in particular act as an agonist, or as both an antagonist and an agonist, in particular an agonistic or an antagonistic effect, depending on the selected modulator concentration selected an "agonist” is a compound that mediates an activation of the TRPM8 receptor , So induces a Ca 2+ influx into the cold-sensitive neurons, thus giving a feeling of cold.
  • an "antagonist” is a compound which can counteract this activation of the TRPM8 receptor
  • the mediators according to the invention can exert their effect by reversibly or irreversibly, specifically or non-specifically binding to a TRPM8 receptor molecule. covalently via ionic and / or nonionic, such as hydrophobic, interactions with the receptor molecule.
  • "Specifically” encompasses both exclusive interaction with one or more different TRPM8 receptor molecules (such as TRPM8 molecules of different origin or different isoforms).
  • an interaction of the modulator with several different receptor molecules of different function and / or sequence is "unspecific", but as a consequence a desired agonistic and / or antagonistic modulation (as described above) of the TRPM8 receptor can be determined.
  • Standard conditions in a cellular activity test for modulators according to the invention is meant in this context an activity test carried out with HEK293 cells which have been transformed with human TRPM8 and loaded with calcium-sensitive dye (such as fluo-4AM, ie fluo-4 Acetoxymethyl ester), subsequent addition of the test compound and detection of the color change, whereby the experiment is carried out at 37 ° C., as described, for example, in Reference Example 3, below, or in Behrendt et al (2004) supra).
  • calcium-sensitive dye such as fluo-4AM, ie fluo-4 Acetoxymethyl ester
  • a “modified form” or “derivative” of a modulator according to the invention is also referred to as a "functional analog” or “functionally equivalent compound", especially if they continue to exhibit the desired biological activity (receptor TRPM8 modulation)
  • the invention also relates to compounds which permit coupling of the specifically disclosed substances to solid supports, a large selection of corresponding linker / spacer groups being known to the person skilled in the art, in which derivatization can take place before coupling to a solid phase or only through the Coupling done.
  • a modulator according to the invention is used, in particular, for inducing cold feelings in humans and / or animals.
  • An "induction of cold sensation” is present when the compound exhibits an agonistic effect on hTRPM8 in the cellular activity assay described above.
  • compositions according to the invention comprise, in addition to the constituents customary for the particular composition, an effective amount of at least one modulator according to the invention.
  • Effective in this context means a concentration of the modulator which is sufficient to achieve the desired effect when the composition is applied (eg application to the skin). such as pharmacological effect, or sensory effect such as mediate the olfactory cold effect.
  • a “topical” application includes, in particular, cutaneous or oral forms of application
  • halogen F, Cl, Br or J.
  • Alkyl and all alkyl moieties in radicals derived therefrom such as, B.
  • C 1 -C 6 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2- Trimethylpropyl, 1-ethyl-1-methylprop
  • C 1 -C 6 alkoxy including C 1 -C 4 alkoxy, such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy;
  • Alkenyl mono- or polysubstituted, in particular monounsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6, 2 to 8 2 to 10 or 2 or to 20 carbon atoms and a double bond in any position, for. B.
  • C 2 -C 6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1 propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3 Methyl 3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl,
  • Halo (gen) alkyl straight-chain or branched alkyl groups having 1 to 4, 1 to 6, 1 to 8, 1 to 10 or 1 to 20 carbon atoms (as mentioned above), wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as above may be replaced, for.
  • B. C 1 -C 2 haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,
  • Chlorofluoromethyl dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-Chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1-trifluoroprop-2-yl.
  • Haloalkoxy for an alkoxy radical having 1 to 8, in particular 1 to 6 and especially 1 to 4 carbon atoms as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, preferably by fluorine, ie z.
  • Cycloalkyl carbocyclic radicals having from 3 to 20 carbon atoms, such as, for example, C 3 -C 12 -cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl and cyclododecyl; preferred are cyclopentyl, cyclohexyl, cycloheptyl and also cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl or C 3 -C 7 -cycloalkyl, such as cyclopropyl, cyclobutyl, Cyclopentyl, cyclohex
  • Cycloalkenyl monocyclic, monounsaturated hydrocarbon groups having from 5 to 8, preferably to 6 carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl and cyclohexen-4-yl;
  • Alkylene straight-chain or mono- or poly-branched hydrocarbon bridging groups having 1 to 20 carbon atoms, such as, for example, C 1 -C 7 -alkylene groups selected from -CH 2 -, - (CH 2 ) 2 -, - (CH 2 ) 3 -, - (CH 2 ) 4 -, - (CH 2 ) 2 -CH (CH 3 ) -, -CH 2 -CH (CH 3 ) -CH 2 -, (CH 2 ) 4 -, - (CH 2 ) 5 - , - (CH 2 ) 6 , - (CH 2 ) 7 -, -CH (CH 3 ) -CH 2 -CH 2 -CH (CH 3 ) - or -CH (CH 3 ) -CH 2 -CH 2 -CH 2 -CH (CH 3 ) - or CC 4 -alkylene groups selected from -CH 2 -, - (CH 2 ) 2
  • Aryl mononuclear or polynuclear, preferably mononuclear or binuclear, optionally substituted aromatic residues of 6 to 20, e.g. From 6 to 10 ring carbon atoms, e.g. Phenyl, biphenyl, naphthyl such as 1- or 2-naphthyl, tetrahydronaphthyl, fluorenyl, indenyl and phenanthrenyl. These aryl radicals may optionally carry 1, 2, 3, 4, 5 or 6 identical or different substituents.
  • Arylalkyl the aryl-substituted analogs of the above alkyl radicals, wherein aryl also has the abovementioned meanings, such as phenyl-C 1 -C 4 -alkyl radicals selected from phenylmethyl or phenyl-ethyl.
  • Aryloxy the oxygen-linked analogs of the above optionally substituted aryl radicals.
  • Heterocyclyl five to seven-membered saturated, partially unsaturated or aromatic heterocycles or heterocyclyl radicals containing one, two, three or four heteroatoms from the group O, N or S.
  • the following subgroups may be mentioned
  • 2-imidazolyl, 4-imidazolyl, and 1, 3,4-triazol-2-yl; 5-membered aromatic heterocyclyl ( heteroaryl or hetaryl) which has 1, 2, 3 or 4 nitrogen atoms as ring members, such as 1-, 2- or 3-pyrrolyl, 1-, 3- or 4-pyrazolyl, 1-, 2- or 4-imidazolyl, 1,2,3- [1 H] -triazol-1-yl, 1,2,3- [2H] -triazol-2-yl, 1, 2,3- [1H] triazol-4-yl,
  • 1,2,4-thiadiazol-3-yl, 1, 2,4-thiadiazol-5-yl, 1, 3,4-thiadiazol-2-yl, 1, 2,4-oxadiazol-3-yl, 1, 2, 4-oxadiazol-5-yl and 1, 3,4-oxadiazol-2-yl; - 6-membered heterocyclyl ( heteroaryl or hetaryl), containing in addition to carbon atoms one or two or one, two or three nitrogen atoms as ring members, for. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl,
  • Heteroaryloxy or heteroaryloxy stands for the oxygen-linked analogs above heterocyclyl or heteroaryl radicals.
  • Substituents in particular those of the above radicals, are in particular selected from keto groups, -COOH, -COO-alkyl, -OH, -SH, -CN, amino, -NO 2 , alkyl, or alkenyl groups, where in the alkyl or alkenyl groups one or more H atoms can be replaced by halogen.
  • R 11 , R 12 and R 13 are selected independently of each other under:
  • X and Z are independently selected under
  • R 21 and R 22 are independently selected from:
  • R23 is selected under:
  • mononuclear or polynuclear aryl, arylalkyl and heteroaryl groups which optionally carry 1, 2, 3 or 4 identical or different substituents which are selected from NH 2 , OH, SH, halogen, straight-chain or branched C 1 -C 6 -alkyl groups and straight or branched C 1 -C 6 alkyloxy groups; wherein the heteroaryl groups have 1, 2, 3 or 4 ring heteroatoms which are the same or different and are selected from O, N and S;
  • X is selected from O, S or methylene
  • Y is selected from N or CH;
  • Z is selected from O, S or NR 24 , where
  • R 24 is H; or a straight-chain or branched C 1 -C 6 -alkyl group which optionally carries 1, 2, 3 or 4 identical or different substituents which are selected from among NH 2 , OH, SH, halogen or straight-chain or branched C 1 -C 6 - alkoxy groups; or R 24 and R 2 3 together with the Z group to which they are attached form a 4-, 5-, 6- or 7-membered, saturated, or mono- or polyunsaturated heterocyclic ring which optionally contains 1, 2, 3, 4 or 5 bear identical or different substituents selected from straight-chain or branched C 1 -C 6 -alkyl groups and having 1, 2 or 3 additional ring heteroatoms which are identical or different and are selected from O , N and S; and salts of these compounds, in particular acid addition salts with inorganic or especially organic, mono- or especially polybasic carboxylic acids; optionally in stereoisomerically pure form or as a mixture of stereoisomers; and where appropriate,
  • R31, R32, R33, R34 and R35 are identical or different and are selected from
  • straight-chain or branched C 1 -C 6 -alkyl groups which optionally carry 1, 2, 3 or 4 identical or different substituents which are selected from among NH 2 , OH, SH, halogen or straight-chain or branched C 1 -C 6 -alkoxy groups; straight-chain or branched C 1 -C 6 -alkoxy groups which optionally carry 1, 2, 3 or 4 identical or different substituents which are selected from among NH 2 , OH, SH, halogen or C 1 -C 6 -alkoxy groups;
  • mononuclear or polynuclear aryl, arylalkyl and heteroaryl groups which optionally carry 1, 2, 3 or 4 identical or different substituents which are selected from NH 2 , OH, SH, halogen, straight-chain or branched C 1 -C 6 -alkyl groups and straight or branched C 1 -C 6 alkyloxy groups; wherein the heteroaryl groups have 1, 2, 3 or 4 ring heteroatoms which are the same or different and are selected from O, N and S; or
  • R 31 , R 32 , R 33 , R 34 and R 35 together with the carbon atoms to which they are attached form a 4-, 5-, 6- or 7-membered, mono- or polyunsaturated heterocyclic ring, the optionally 1, 2, 3, 4 or 5 bear identical or different substituents which are selected from straight-chain or branched C 1 -C 6 -alkyl groups and which has 1, 2 or 3 ring heteroatoms which are identical or different and selected are below O, N and S; and R 37 are the same or different and selected from:
  • X is selected under -C 1 -C 4 alkylene groups; -C 2 -C 4 alkenylene groups, and also -Z-C 1 -C 4 or -C 1 -C 4 -Z-alkylene groups or -ZC 2 -C 4 - or - C 2 -C 4 -Z-alkenylene groups, wherein Z is O , S or NH; or represents a single chemical bond; and salts of these compounds, in particular acid addition salts with inorganic or especially organic, mono- or especially polybasic carboxylic acids; optionally in stereoisomerically pure form or as a mixture of stereoisomers; and where appropriate, the compounds having the structure
  • Use of a compound as defined in embodiment 1, for inducing a feeling of coldness in a packaging for example of paper or plastic in various processing forms (such as fibers, fabrics, moldings), wherein the feeling of cold especially in contact with the packaging material noticeable.
  • the substances may be associated with the packaging material in many different ways: for example by spin coating, printing, in the form of microencapsulation, direct incorporation into the packaging material (eg extruding), covalent coupling of suitable derivatives of the modulators (via suitable spacer / linker groups, by means of which the molecule is bound reversibly or irreversibly to the packaging material). Suitable procedures are known in the art. Use of a compound as defined in Embodiment 1 to induce a feeling of coldness in a textile.
  • the substances may be associated with the textile in many different ways: for example by spin coating, printing, in the form of microencapsulation, direct incorporation into the textile material (eg extruding), covalent coupling of suitable derivatives of the modulators (via suitable spacer / linker groups, by means of which the molecule is bound reversibly or irreversibly to the packaging material). Suitable procedures are known in the art.
  • compounds of structure type 3 are suitable as UV absorbers, so that, for example, a combined use of this compound as UV absorber and cooling agent, for example in sun creams, is particularly advantageous.
  • Means comprising at least one compound according to embodiment 1.
  • a) pharmaceutical agents such as antitumor agents, agents for the treatment of bladder disorders, analgesics;
  • foods such as ice cream, mousse, cream, beverages, sweets;
  • oral care products such as toothpaste, mouthwash, chewing gum
  • breath freshener d) body care products, such as skin or hair care products, such as sunscreen, sunburn cream, lotions, shampoos, shaving cream, conditioner, facial cleanser, soaps, bath oils and bath foams, antiperspirants, deodorants,
  • a product comprising at least one compound according to embodiment 1, selected from
  • a) textile products e.g. Shirts, pants, socks, towels,
  • keto group is linked to the molecule via the R 12 or in particular via the Rn position.
  • R 21 is a straight-chain or branched C 1 -C 6 -alkyl group; or is a mononuclear aryl, arylalkyl and heteroaryl group, wherein the heteroaryl group has 1 or 2 ring heteroatoms which are identical or different and are selected from O, N and S;
  • R 22 is H, a straight-chain or branched C 1 -C 6 -alkyl group; or is a mononuclear aryl, arylalkyl and heteroaryl group, wherein the heteroaryl group has 1 or 2 ring heteroatoms which are identical or different and are selected from O, N and S;
  • R 22 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl or phenyl, in particular H;
  • R 23 is selected from straight-chain or branched C 1 -C 6 -alkyl groups which optionally carry 1 or 2 identical or different substituents selected from among NH 2 , OH, SH, halogen or straight-chain or branched C C 1 -C 6 alkoxy groups; C 3 -C 7 cycloalkyl groups, wherein the cycloalkyl group is optionally bonded to Z via a C 1 -C 4 alkylene group, and optionally wherein 1, 2 or 3 ring carbon atoms are represented by identical or different heteroatoms selected from O, N and S can be replaced; mononuclear aryl, arylalkyl and heteroaryl groups, where the heteroaryl groups 1, or 2 ring Have heteroatoms which are the same or different and are selected from O, N and S;
  • R 2 3 is selected from straight-chain or branched C 1 -C 6 -alkyl groups which optionally carry 1 substituent selected from OH or straight-chain or branched C 1 -C 3 -alkoxy groups; C 3 -C 7 -cycloalkyl groups wherein the cycloalkyl group is optionally bonded to Z via a C 1 -C 4 -alkylene group, and optionally wherein 1 or 2 ring carbon atoms may be replaced by identical or different heteroatoms selected from O and N;
  • cyclobutyl in particular cyclobutyl, cyclopentyl, i-propyl, sec-butyl, 3-methylbut-2-yl, 1-methoxy-prop-2-yl; 1-hydroxybut-3-yl, cyclopropylmethyl,
  • Acid addition salts of compounds of formula II, in particular of embodiments (1) to (57), when Z comprises a protonated N-atom, with organic mono- or polycarboxylic acids (60) acid addition salts of compounds of formula II, in particular of the embodiments (1) to (57) when Z comprises a protonated N atom with organic mono- or polycarboxylic acids, wherein the carboxylic acid is selected from saturated or mono- or polyunsaturated C 1 -C 30 monocarboxylic acids, saturated or mono- or poly- polyunsaturated C 3 -C 10 -di or tricarboxylic acids, wherein the carboxylic acid may be mono- or polysubstituted by hydroxy groups;
  • R 35 is H or halo
  • R 31 is H, halogen, a straight-chain or branched C 1 -C 6 -alkyl group which optionally carries 1, 2, 3 or 4 identical or different substituents which are selected from NH 2 , OH, SH, halogen or straight-chain or branched C 1 -C 6 -alkoxy groups; or a straight-chain or branched C 1 -C 6 -
  • Alkoxy group optionally bearing 1, 2, 3 or 4 identical or different substituents selected from NH 2 , OH, SH, halogen or C 1 -C 6 alkoxy groups; (4) compounds of formula III wherein R 31 is H, halogen, a straight or branched C 1 -C 6 alkyl group; or a straight-chain or branched C 1 -C 6 -alkoxy group;
  • R 31 is H, methyl, ethyl, methoxy, ethoxy, or halogen, in particular H, fluorine, chlorine, bromine, methyl or methoxy;
  • Alkoxy groups optionally bearing 1, 2, 3 or 4 identical or different substituents selected from NH 2 , OH, SH, halogen or C 1 -C 6 alkoxy groups; (7) compounds of the formula III in which the radicals R 32 and R 33 are identical or different and are selected from H, halogen, straight-chain or branched C 1 -C 6 -alkyl groups; or straight-chain or branched C 1 -C 6 -alkoxy groups;
  • radicals R 36 and R 37 are identical or different and are selected from straight-chain or branched C 1 -C 6 -alkyl groups which optionally carry 1 or 2 identical or different substituents which are selected from NH 2 , OH , SH, halogen or straight-chain or branched C 1 -C 6 -alkoxy groups; mononuclear aryl, arylalkyl and heteroaryl groups, optionally
  • the active compounds according to the invention have a broad field of application in the field of human cosmetics and care, in particular skin and hair care, but can also be used pharmacologically, as well as in foodstuffs and textile products, but also as repellents and as components of insecticidal compositions.
  • the agents according to the invention may be, in particular, skin-cosmetic, hair-cosmetic, dermatological, hygienic or pharmaceutical agents.
  • the active ingredients according to the invention in particular cooling agents, are used for dermal and / or hair cosmetics or as oral hygiene products.
  • the hair- or skin-care preparations according to the invention are in particular in the form of an emulsion, a dispersion, a suspension, in the form of an aqueous surfactant preparation, a milk, a lotion, a cream, a balm, an ointment, a gel, a granulate, a powder, a pencil preparation, such as.
  • a lipstick, a foam, an aerosol or a spray before Such formulations are well suited for topical preparations.
  • Suitable emulsions are oil-in-water emulsions and water-in-oil emulsions or microemulsions.
  • the hair or skin cosmetic preparation is used for application to the skin (topically) or to the hair.
  • Topical preparations are to be understood as meaning those preparations which are suitable for applying the active substances to the skin in finely distributed form, for example in a form absorbable by the skin, for example aqueous and aqueous-alcoholic solutions , Sprays, foams, foam aerosols, ointments, aqueous gels, emulsions of the O W or W / O type, microemulsions or cosmetic stick preparations.
  • this contains a carrier.
  • Preferred as a carrier is water, a gas, a water-based liquid, an oil, a gel, an emulsion or microemulsion, a dispersion or a mixture thereof.
  • the mentioned carriers show good skin tolerance.
  • Particularly advantageous for topical preparations are aqueous gels, emulsions or microemulsions.
  • the teaching of the invention also encompasses the use of the active ingredients described herein in pharmaceutical agents for treating an individual, preferably a mammal, especially a human, animal or pet.
  • the active compounds are administered in the form of pharmaceutical compositions comprising a pharmaceutically acceptable excipient with at least one active ingredient according to the invention and optionally other active ingredients.
  • These compositions may be administered by, for example, oral, rectal, transdermal, subcutaneous, intravenous, intramuscular or intranasal routes.
  • suitable pharmaceutical formulations are solid dosage forms such as powders, powders, granules, tablets, lozenges, sachets, cachets, dragees, capsules such as hard and soft gelatin capsules, suppositories or vaginal dosage forms, semisolid dosage forms such as ointments, creams, hydrogels, pastes or patches , as well as liquid dosage forms, such as solutions, emulsions, in particular oil-in-water emulsions, suspensions, for example lotions, injection and infusion preparations, eye and ear drops. Implanted delivery devices may also be used to deliver inhibitors of the invention. Furthermore, liposomes, microspheres or polymer matrices can also be used.
  • active compounds according to the invention are usually mixed or diluted with an excipient.
  • Excipients may be solid, semi-solid or liquid materials which serve as a vehicle, carrier or medium for the active ingredient.
  • the active ingredient content (of one or more simultaneously contained active substances according to the invention) can vary within a wide range and is approximately, in each case based on the total weight of the composition, in the ppm range of about 0.05 ppm - ⁇ 0.1 ppm and 0 , 1 to 1000 ppm (ie, 0.00001 to 0, 1 wt .-%), such as 1 to 800 ppm or 100 to 500 ppm or in the range of 0, 1 to 50, 1 to 30 or 2 to 10 wt .-%.
  • Suitable excipients include, for example, lactose, dextrose, sucrose, sorbitol, mannitol, starches, acacia, calcium phosphate, alginates, tragacanth, gelatin, calcium silicate, microcrystalline cellulose, polyvinylpyrrolidone, cellulose, water, syrup, and methyl cellulose.
  • the formulations may include pharmaceutically acceptable carriers or conventional adjuvants such as lubricants, for example, tallow, magnesium stearate and mineral oil; Network- medium; emulsifying and suspending agents; preservatives such as methyl and propyl hydroxybenzoates; antioxidants; Antiirritatives; chelating agents; coating aids; Emulsion stabilizers film former; gelling agents; Odor masking agents; masking flavors; resins; Hydrocolloids; Solvents; Solubilizing agents; Neutralizing agents; permeation; pigments; quaternary ammonium compounds; Refatting and superfatting agents; Ointment, cream or oil bases; Silicone derivatives; spreading aids; stabilizers; Sterilanzien; suppository bases; Tablet excipients such as binders, fillers, lubricants, disintegrants or coatings; Propellant; Desiccant; Opacifiers; Thickener; waxes; plasticizers; Include white oils.
  • compositions according to the invention may contain, in addition to customary additives or excipients, additionally cosmetically and / or dermatologically and / or pharmacologically active substances.
  • Suitable cosmetically and / or dermatologically active agents are, for.
  • Artificial tanning agents suitable for tanning the skin without natural or artificial exposure to UV rays are z. Dihydroxyacetone, alloxan and walnut shell extract. Suitable keratin-hardening substances are as a rule active ingredients, as are also used in antiperspirants, such as. As potassium aluminum sulfate, aluminum hydroxychloride, aluminum lactate, etc. Antimicrobial agents that are used to destroy microorganisms or to inhibit their growth. They thus serve both as a preservative and as a deodorizing substance, which reduces the formation or intensity of body odor. These include z. B.
  • auxiliaries and additives are preferably cosmetically and / or pharmaceutically acceptable auxiliaries.
  • Suitable adjuvants may include lubricants, wetting agents, emulsifying and suspending agents, preservatives, antioxidants, anti-irritants, chelating agents, emulsion stabilizers, film formers, gelling agents, odor masking agents, hydrocolloids, solvents, solubilizers, neutralizing agents, permeation enhancers, pigments, quaternary ammonium compounds, refatting and superfatting agents , Ointment, cream or oil bases, silicone derivatives, stabilizers, sterilizers, blowing agents, drying agents, opacifiers, thickeners, waxes, plasticizers, white oil.
  • a related embodiment is based on expert knowledge, as shown for example in Fiedler, HP Lexicon of excipients for pharmacy, cosmetics and related fields, 4th ed., Aulendorf: ECV Editio-Kantor-Verlag, 1996.
  • Suitable additives are selected from perfume oils, hair polymers, hair and skin conditioners, graft polymers, water-soluble or dispersible silicone-containing polymers, light stabilizers, bleaches, conditioners, colorants, tints, tanning agents, dyes, bodying agents, moisturizers, restockers, collagen, protein hydrolysates, lipids, antioxidants Defoamers, antistatic agents, emollients, plasticizers, peroxide decomposers.
  • auxiliaries and additives include: (1) antioxidants selected from amino acids (eg, glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (eg, urocanic acid) and their derivatives, peptides such as D, L Carnosine, D-carnosine, L-carnosine and their derivatives (eg anserine), carotenoids, carotenes (eg .beta.-carotene, lycopene) and their derivatives, chlorogenic acid and their derivatives, lipoic acid and its derivatives (eg dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (eg, thiorodoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl , Propyl, amyl, butyl, and lauryl, palmio
  • Vitamin A acetate, tocotrienol
  • vitamin A and derivatives vitamin A palmitate
  • Peroxide decomposers d. H. Compounds capable of decomposing peroxides, more preferably lipid peroxides. These include organic substances, such as. As pyridine-2-thiol-3-carboxylic acid, 2-methoxy-pyrimidinol-carboxylic acids, 2-methoxy-pyridinecarboxylic acids, 2-dimethylamino-pyrimidinolcarbonklaren, 2-Dimethylamino- pyridincarbonklaren.
  • Thickeners such as crosslinked polyacrylic acids and their derivatives, polysaccharides and their derivatives, such as xanthan gum, agar-agar, alginates or Tyloses, cellulose derivatives, eg. As carboxymethylcellulose or hydroxycarboxymethylcellulose, fatty alcohols, monoglycerides and fatty acids, polyvinyl alcohol and polyvinylpyrrolidone. In particular, nonionic thickeners are used.
  • preservatives or preservatives are cosmetics, such as dibromodicyanobutane (2-bromo-2-bromomethyl-glutarodinitrile), 3-iodo-2-propynyl-butylcarbamate, 2-bromo-2-nitro-propane-1,3-diol, Imidazolidinylurea, 5-chloro-2-methyl-4-isothiazolin-3-one, 2-chloroacetamide, benzalkonium chloride, benzyl alcohol, formaldehyde releaser.
  • cosmetics such as dibromodicyanobutane (2-bromo-2-bromomethyl-glutarodinitrile), 3-iodo-2-propynyl-butylcarbamate, 2-bromo-2-nitro-propane-1,3-diol, Imidazolidinylurea, 5-chloro-2-methyl-4-isothiazolin-3-one, 2-chloroacetamide,
  • phenylhydroxyalkyl ethers in particular the compound known by the name phenoxyethanol, are suitable as preservatives because of their bactericidal and fungicidal effects on a number of microorganisms.
  • germ-inhibiting agents are also suitable for incorporation into the preparations according to the invention.
  • Advantageous substances are, for example, 2,4,4'-trichloro-2'-hydroxydiphenyl ether (Irgasan), 1, 6-di (4-chlorphenylbiguanido) hexane (Chlorhexidine), 3,4,4'-trichlorocarbanilide, quaternary ammonium compounds, clove oil, mint oil, thyme oil, triethyl citrate, farnesol (3,7, 1 1-trimethyl-2, 6,10-dodecatrien-1-ol) and the in the patent publications DE-37 40 186, DE-39 38 140, DE-42 04 321, DE-42 29 707, DE-43 09 372, DE-44 1 1 664, DE-195 41 967, DE-195 43 695 , DE-195 43 696, DE-195 47 160, DE-196 02 108, DE-196 02 1 10, DE-196 02 1 1 1, DE-196 31
  • UV filters that absorb UV rays in the UV-B and / or UV-A range.
  • Suitable UV filters are z. B. 2,4,6-triaryl-1, 3,5-triazines in which the aryl groups may each bear at least one substituent, which is preferably selected from hydroxy, alkoxy, especially methoxy, alkoxycarbonyl, especially methoxycarbonyl and ethoxycarbonyl, and mixtures from that.
  • substituent which is preferably selected from hydroxy, alkoxy, especially methoxy, alkoxycarbonyl, especially methoxycarbonyl and ethoxycarbonyl, and mixtures from that.
  • p-aminobenzoic acid esters cinnamic acid esters, benzophenones, camphor derivatives and UV-radiation-stopping pigments, such as titanium dioxide, talc and zinc oxide.
  • Suitable UV filter substances are any UV-A and UV-B filter substances.
  • UV-A and UV-B filter substances are any UV-A and UV-B filter substances.
  • the cosmetic and dermatological preparations according to the invention can advantageously also UV-retardant inorganic pigments based on metal oxides and / or other sparingly soluble or insoluble in water metal compounds selected from the group of oxides of zinc (ZnO), titanium (Ti0 2 ), iron (eg Fe 2 O 3 ), zirconium (ZrO 2 ), silicon (SiO 2 ), manganese (eg MnO), aluminum (Al 2 O 3 ), cerium (eg Ce 2 0 3 ), mixed oxides the corresponding metals and mixtures of such oxides.
  • the inorganic pigments can be present in coated form, d. H. that they are superficially treated.
  • This surface treatment can be, for example, that the pigments are provided in a manner known per se, as described in DE-A-33 14 742, with a thin hydrophobic layer.
  • Repellent agents d. H. Compounds capable of preventing or repelling certain animals, especially insects. This includes z. B. 2-ethyl-1, 3-hexanediol, N, N-diethyl-m-toluamide, etc.
  • Suitable hyperemic substances which stimulate the circulation of the skin are, for.
  • Essential oils such as mountain pine extract, lavender extract, rosemary extract, juniper berry extract, horse chestnut extract, birch leaf extract, hay flower extract, ethyl acetate, camphor, menthol, peppermint oil, rosemary extract, eucalyptus oil, etc.
  • Suitable keratolytic and keratoplastic substances are for.
  • salicylic acid calcium thioglycolate, thioglycolic acid and its salts, sulfur, etc.
  • Suitable antishock agents are z. Sulfur, sulfur polyethyleneglycol sorbitan monooleate, sulfur ricinol polyethoxylate, zinc pyrithione, aluminum pyrithione, etc.
  • Suitable anti-inflammatory drugs that counteract skin irritation, z. Allantoin, bisabolol, dragosantol, chamomile extract, panthenol, etc.
  • Cosmetically or pharmaceutically acceptable polymers such as cationic, amphoteric and neutral polymers.
  • Suitable polymers are, for. B. cationic polymers called polyquaternium according to INCI, z. B. Copolymers of vinylpyrrolidone / N-vinylimidazolium salts (Luviquat FC, Luviquat HM, Luviquat MS, Luviquat Care), copolymers of N-vinylpyrrolidone / dimethylaminoethyl methacrylate, quaternized with diethyl sulfate (Luviquat PQ 11), copolymers of N-vinylcaprolactam / N-vinylpyrrolidone / N-vinylimidazolium salts (Luviquat E Hold), cationic cellulose derivatives (Polyquaternium-4 and -10), acrylamidocopolymers (Polyquaternium-7) and chitosan.
  • Suitable cationic (quaternized) polymers are also merquat (polymer based on dimethyldiallyl ammonium chloride), gafquat (quaternary polymers formed by reaction of polyvinylpyrrolidone with quaternary ammonium compounds), polymer JR (hydroxyethylcellulose with cationic groups) and cationic polymers based on plants, e.g. As guar polymers, such as the Jaguar brands of Rhodia.
  • polystyrene resins are also neutral polymers, such as polyvinylpyrrolidones, copolymers of N-vinylpyrrolidone and vinyl acetate and / or vinyl propionate, polysiloxanes, polyvinylcaprolactam and other copolymers with N-vinylpyrrolidone, polyethyleneimines and their salts, polyvinylamines and their salts, cellulose derivatives, polyaspartic acid salts and derivatives thereof , These include, for example, Luviflex® swing (partially saponified copolymer of polyvinyl acetate and polyethylene glycol, BASF).
  • Luviflex® swing partially saponified copolymer of polyvinyl acetate and polyethylene glycol, BASF.
  • Suitable polymers are also nonionic, water-soluble or water-dispersible polymers or oligomers, such as polyvinyl caprolactam, z. B. Luviskol ® Plus (BASF), or polyvinylpyrrolidone and their copolymers, in particular with vinyl esters, such as vinyl acetate, z. B. Luviskol ® VA 37 (BASF), polyamides, z. B. based on itaconic acid and aliphatic diamines, as z. B. in DE-A-43 33 238 are described.
  • nonionic, water-soluble or water-dispersible polymers or oligomers such as polyvinyl caprolactam, z. B. Luviskol ® Plus (BASF), or polyvinylpyrrolidone and their copolymers, in particular with vinyl esters, such as vinyl acetate, z. B. Luviskol ® VA 37 (BASF), polyamides, z. B. based on itac
  • Suitable polymers are also amphoteric or zwitterionic polymers, such as those available under the names Amphomer (National Starch) octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate hydroxypropyl methacrylate copolymers and zwitterionic polymers, as described for example in German patent applications DE39 29 973, DE 21 50 557, DE28 17 369 and DE 3708 451 are disclosed.
  • Acrylamidopropyltrimethylammonium chloride / acrylic acid or methacrylic acid copolymers and their alkali metal and ammonium salts are preferred zwitterionic polymers.
  • zwitterionic polymers are methacroylethylbetaine / methacrylate copolymers, which are commercially available under the name Amersette (AMERCHOL), and copolymers of hydroxyethyl methacrylate, methyl methacrylate, N, N-dimethylaminoethyl methacrylate and acrylic acid (Jordapon (D)).
  • Suitable polymers are also nonionic, siloxane-containing, water-soluble or dispersible polymers, for.
  • polyether siloxanes such as Tegopren ® (Goldschmidt) or Besi (Wacker).
  • the agents according to the invention are a cooling skin or hair care or cleansing agent.
  • Preferred skin or hair cleansing preparations are soaps of liquid to gelatinous consistency, such as transparent soaps, luxury soaps, de-soaps, cream soaps, baby soaps, skin protectants, abrasive soaps and syndets, pastose soaps, soft soaps and washing pastes, peeling soaps, moist wipes, liquid washing, showering and bath preparations, such as washing lotions, shower baths and gels, bubble baths, oil baths and scrub preparations, shaving foams, lotions and creams.
  • the agents according to the invention are a shower gel, a shampoo formulation or a bathing preparation.
  • Such formulations contain at least one active ingredient according to the invention and usually anionic surfactants as base surfactants and amphoteric and / or nonionic surfactants as cosurfactants.
  • suitable active ingredients and / or adjuvants are generally selected from lipids, perfume oils, dyes, organic acids, preservatives and antioxidants, as well as thickeners / gelling agents, skin conditioners and humectants.
  • the active ingredient content can be over a wide range, e.g. 0.00001 to 50 wt .-%, in particular 0.001 to 10 wt .-% or 0.005 to 1 wt .-% vary.
  • Suitable skin cosmetic agents are, for.
  • Means for use in decorative cosmetics include, for example, masking pens, theatrical paints, mascara and eye shadows, lipsticks, kohl pencils, eyeliners, rouges, powders, and eyebrow pencils.
  • the dermatological compositions of the present invention may be used in nasal strips for pore cleansing, in anti-acne agents, repellents, shaving agents, after- and pre-shave conditioners, after-sun conditioners, depilatories, hair colorants, personal care products, foot care products, and baby care.
  • the skin care compositions according to the invention are in particular W / O or O / W skin creams, day and night creams, eye creams, face creams, anti-wrinkle creams, sunscreen creams, moisturizing creams, bleaching creams, self-tanning creams, vitamin creams, skin lotions, body lotions and moisturizing lotions.
  • Skin cosmetic and dermatological agents contain in particular at least one active ingredient according to the invention in a proportion of about 0.0001 to 50 wt .-%, such as. B. 0.001 to 10 wt .-%, in particular 0.005 to 0, 1 wt .-%, based on the total weight of the composition.
  • the skin cosmetics according to the invention may be in a form suitable for skin care, such as. B. as cream, foam, gel, pen, mousse, milk, spray (pump spray or propellant spray) or lotion can be applied.
  • the skin cosmetic preparations may contain further active ingredients and auxiliaries customary in skin cosmetics, as described above. These preferably include emulsifiers, preservatives, perfume oils, cosmetic active ingredients such as phytantriol, vitamins A, E and C, retinol, bisabolol, panthenol, light stabilizers, bleaching agents, colorants, tinting agents, tanning agents, collagen, enzymes, protein hydrolysates, stabilizers, pH regulators , Dyes, salts, thickeners, gelling agents, bodying agents, silicones, humectants, moisturizers and other common additives.
  • active ingredients and auxiliaries customary in skin cosmetics as described above. These preferably include emulsifiers, preservatives, perfume oils, cosmetic active ingredients such as phytantriol, vitamins A, E and C, retinol, bisabolol, panthenol, light stabilizers, bleaching agents, colorants, tinting agents, tanning agents, collagen, enzymes, protein
  • Preferred oil and fat components of the skin cosmetic and dermatological agents are the aforementioned mineral and synthetic oils, such as.
  • the skin cosmetic and dermatological preparations may additionally contain conditioning substances based on silicone compounds.
  • suitable Silicone compounds are, for example, polyalkylsiloxanes, polyarylsiloxanes, polyarylalkylsiloxanes, polyethersiloxanes or silicone resins.
  • the preparation of the cosmetic or dermatological preparations is carried out by customary methods known to the person skilled in the art.
  • the active ingredients may be mixed or diluted with a suitable excipient (excipient).
  • Excipients may be solid, semi-solid or liquid materials which may serve as a vehicle, carrier or medium for the active ingredient. If desired, the admixing of further auxiliaries takes place in the manner known to the person skilled in the art.
  • the polymers and dispersions are suitable, as auxiliaries in pharmacy, preferably as or in coating agent (s) or binder (s) for solid dosage forms. They can also be used in creams and as tablet coatings and tablet binders.
  • the cosmetic and dermatological agents are preferably in the form of emulsions, in particular as water-in-oil (W / O) or oil-in-water (O / W) emulsions.
  • W / O water-in-oil
  • O / W oil-in-water
  • emulsifier-free Formulations such as hydrodispersions, hydrogels or a Pickering emulsion are advantageous embodiments.
  • Emulsions are prepared by known methods.
  • the emulsions generally contain customary constituents, such as fatty alcohols, fatty acid esters and especially fatty acid triglycerides, fatty acids, lanolin and derivatives thereof, natural or synthetic oils or waxes and emulsifiers in the presence of water.
  • customary constituents such as fatty alcohols, fatty acid esters and especially fatty acid triglycerides, fatty acids, lanolin and derivatives thereof, natural or synthetic oils or waxes and emulsifiers in the presence of water.
  • a skin cream, etc. generally contains an aqueous phase which is emulsified by means of a suitable emulsifier in an oil or fat phase.
  • a polyelectrolyte complex can be used.
  • Preferred fat components which may be present in the fatty phase of the emulsions are: hydrocarbon oils, such as paraffin oil, purcellin oil, perhydrosqualene and solutions of micro-oils. crystalline waxes in these oils; animal or vegetable oils, such as sweet almond oil, avocado oil, Calophylumöl, lanolin and derivatives thereof, castor oil, sesame oil, olive oil, jojoba oil, karite oil, Hoplostethus oil, mineral oils whose distillation begins under atmospheric pressure at about 250 ° C and their distillation endpoint at 410 ° C is such.
  • As Vaselineöl esters of saturated or unsaturated fatty acids, such as alkyl myristates, z.
  • i-propyl, butyl or cetyl myristate hexadecyl stearate, ethyl or i-propyl palmitate, octanoic or Decanklandretriglyceride and Cetylricinoleat.
  • the fat phase may also contain silicone oils soluble in other oils, such as dimethylpolysiloxane, methylphenylpolysiloxane and the silicone glycol copolymer, fatty acids and fatty alcohols.
  • waxes can be used, such as. Carnauba wax, candililla wax, beeswax, microcrystalline wax, ozokerite wax and Ca, Mg and Al oleates, myristates, linoleates and stearates.
  • an emulsion of the invention may be present as an O W emulsion.
  • Such an emulsion usually contains an oil phase, emulsifiers that stabilize the oil phase in the water phase, and an aqueous phase that is usually thickened.
  • Suitable emulsifiers are preferably O / W emulsifiers, such as polyglycerol esters, sorbitan esters or partially esterified glycerides.
  • the agents according to the invention are a shower gel, a shampoo formulation or a bath preparation.
  • Such formulations contain at least one active ingredient according to the invention and usually anionic surfactants as base surfactants and amphoteric and / or nonionic surfactants as cosurfactants.
  • suitable active ingredients and / or adjuvants are generally selected from lipids, perfume oils, dyes, organic acids, preservatives and antioxidants, as well as thickeners / gelling agents, skin conditioners and humectants.
  • formulations contain in particular 2 to 50 wt .-%, such as 5 to 40 wt .-%, or 8 to 30 wt .-% of surfactants, based on the total weight of the formulation.
  • surfactants based on the total weight of the formulation.
  • all anionic, neutral, amphoteric or cationic surfactants commonly used in personal care products can be used.
  • Suitable anionic surfactants are, for example, alkyl sulfates, alkyl ether sulfates, alkyl sulfonates, alkylaryl sulfonates, alkyl succinates, alkyl sulfosuccinates, N-alkoyl sarcosinates, acyl taurates, acyl isothionates, alkyl phosphates, alkyl ether phosphates, alkyl ether carboxylates, alpha-olefin sulfonates, in particular the alkali metal and alkaline earth metal salts, eg. As sodium, potassium, magnesium, calcium, and ammonium and triethanolamine salts.
  • the alkyl ether sulfates, alkyl ether phosphates and alkyl ether carboxylates can have between 1 to 10 ethylene oxide or propylene oxide units, preferably 1 to 3 ethylene oxide units, in the molecule.
  • Suitable amphoteric surfactants are, for. Alkylbetaines, alkylamidopropylbetaines, alkylsulfobetaines, alkylglycinates, alkylcarboxyglycinates, alkylamphoacetates or propionates, alkylamphodiacetates or dipropionates.
  • cocodimethylsulfopropyl betaine, lauryl betaine, cocamidopropyl betaine or sodium cocamphopropionate can be used.
  • Suitable nonionic surfactants are, for example, the reaction products of aliphatic alcohols or alkylphenols having 6 to 20 C atoms in the alkyl chain, which may be linear or branched, with ethylene oxide and / or propylene oxide. The amount of alkylene oxide is about 6 to 60 moles per mole of alcohol.
  • alkylamine oxides are also suitable.
  • mono- or dialkylalkanolamides are also suitable.
  • fatty acid esters of polyethylene glycols are also suitable.
  • ethoxylated fatty acid amides are also suitable.
  • alkylpolyglycosides are also suitable.
  • washing, showering and bathing preparations may contain conventional cationic surfactants, such as. B. quaternary ammonium compounds, such as cetyltrimethyl ammonium chloride.
  • shower gel / Shampooformultechniken thickener such.
  • sodium chloride PEG-55, propylene glycol oleate, PEG-120-methyl glucose dioleate and others and preservatives, other active ingredients and excipients and water.
  • the agents according to the invention are a hair treatment agent.
  • Hair treatment compositions according to the invention contain in particular at least one active ingredient according to the invention in an amount in the range of about 0.0001 to 50 wt .-%, such as 0.001 to 10 wt .-%, in particular 0.005 to 0, 1 wt .-%, based on the total weight of the agent.
  • the hair treatment compositions according to the invention are present in the form of a mousse, hair mousse, hair gel, shampoos, hair sprays, hair mousse, top fluids, permanent wetting, hair dyeing and bleaching agents or hot oil treatments.
  • the hair cosmetic preparations can be applied as (aerosol) spray, (aerosol) foam, gel, gel spray, cream, lotion or wax.
  • Hairsprays include both aerosol sprays and pump sprays without propellant gas.
  • Hair foams include both aerosol foams and pump foams without propellant gas.
  • Hair sprays and hair foams preferably comprise predominantly or exclusively water-soluble or water-dispersible components.
  • the compounds used in the hair sprays and hair foams according to the invention are water-dispersible, they can be used in the form of aqueous microdispersions with particle diameters of usually from 1 to 350 nm, preferably from 1 to 250 nm.
  • the solids contents of these preparations are usually in a range of about 0.5 to 20 wt .-%.
  • these microdispersions do not require emulsifiers or surfactants for their stabilization.
  • the hair cosmetic formulations of the invention contain in a specific embodiment a) 0.0001 to 50 wt .-% or 0.001 to 10, or 0.005 to 1 wt .-% of at least one active ingredient b) 20 to 99.95 wt .-% water and c) 0 to 50% by weight of at least one propellant, d) 0 to 5% by weight of at least one emulsifier, e) 0 to 3% by weight of at least one thickener, and up to 25% by weight. % other ingredients.
  • alcohol all alcohols customary in cosmetics are to be understood, for.
  • ethanol isopropanol, n-propanol.
  • Suitable conventional hair cosmetic polymers include, for example, the abovementioned cationic, anionic, neutral, nonionic and amphoteric polymers, to which reference is hereby made.
  • the preparations may additionally contain conditioning substances based on silicone compounds. Suitable silicone compounds are, for example, polyalkylsiloxanes, polyarylsiloxanes, polyarylalkylsiloxanes, polyethersiloxanes, silicone resins or dimethicone copolyols (CTFA) and amino-functional silicone compounds such as amodimethicones (CTFA).
  • the polymers according to the invention are suitable in particular as setting agents in hairstyling preparations, in particular hairsprays (aerosol sprays and pump sprays without propellant gas) and hair foams (aerosol foams and pump foams without propellant gas).
  • spray formulations contain a) 0.0001 to 50 wt .-% or 0.001 to 10, or 0.005 to 1 wt .-% of at least one active ingredient according to the invention, b) 20 to 99.9 wt .-% water and / or Alcohol, c) 0 to 70% by weight of at least one blowing agent, d) 0 to 20% by weight of further constituents.
  • Blowing agents are the blowing agents commonly used for hairsprays or aerosol foams. Preference is given to mixtures of propane / butane, pentane, dimethyl ether, 1,1-difluoroethane (HFC-152a), carbon dioxide, nitrogen or compressed air.
  • a preferred formulation for aerosol hair foams according to the invention contains a) 0.0001 to 50% by weight or 0.001 to 10, or 0.005 to 1% by weight of at least one active ingredient according to the invention, b) 55 to 99.8% by weight of water and / or alcohol, c) 5 to 20% by weight of a blowing agent, d) 0.1 to 5% by weight of an emulsifier, e) 0 to 10% by weight of further constituents.
  • emulsifiers all emulsifiers commonly used in hair foams can be used. Suitable emulsifiers may be nonionic, cationic or anionic or amphoteric.
  • nonionic emulsifiers are Laurethe, z. Laureth-4; Cetethe, z. Cetheth-1, polyethylene glycol cetyl ether, ceteareth, e.g. Cetheareth-25, polyglycol fatty acid glycerides, hydroxylated lecithin, lactyl esters of fatty acids, alkylpolyglycosides.
  • cationic emulsifiers are cetyldimethyl-2-hydroxyethylammonium dihydrogenphosphate, cetyltrimonium chloride, cetyltrimmonium bromide,
  • Anionic emulsifiers can, for example, be selected from the group of alkyl sulfates, alkyl ether sulfates, alkyl sulfonates, alkylaryl sulfonates, alkyl succinates, alkyl sulfosuccinates, N-alkoyl sarcosinates, acyl taurates, acyl isethionates, alkyl phosphates, alkyl ether phosphates, alkyl ether carboxylates, alpha-olefin sulfonates, in particular the alkali metal and alkaline earth metal salts, eg Sodium, potassium, magnesium, calcium, as well as ammonium and triethanolamine salts.
  • alkali metal and alkaline earth metal salts eg Sodium, potassium, magnesium, calcium, as well as ammonium and triethanolamine salts.
  • the alkyl ether sulfates, alkyl ether phosphates and alkyl ether carboxylates can have between 1 to 10 ethylene oxide or propylene oxide units, preferably 1 to 3 ethylene oxide units in the molecule.
  • a preparation suitable for styling gels according to the invention may for example be composed as follows: a) 0.0001 to 50% by weight or 0.001 to 10, or 0.005 to 1% by weight of at least one active ingredient according to the invention b) 80 to 99.85 % By weight of water and / or alcohol, c) 0 to 3% by weight, preferably 0.05 to 2% by weight, of a gelling agent, d) 0 to 20% by weight of further constituents.
  • gelling agents may be advantageous for adjusting specific rheological or other performance properties of the gels.
  • gel formers all gel formers customary in cosmetics can be used. These include slightly crosslinked polyacrylic acid, for example carbomer (INCI), cellulose derivatives, eg. Hydroxypropyl cellulose, hydroxyethyl cellulose, cationic modified celluloses, polysaccharides, e.g.
  • Xanthan gum caprylic / capric triglyceride, sodium acrylate copolymers, polyquaternium-32 (and) paraffin liquidum (INCI), sodium acrylate copolymers (and) paraffinum liquidum (and) PPG-1 trideceth-6, acrylamidopropyltrimonium chloride / acrylamide copolymers, Steareth-10-allyl ether, acrylate copolymers, polyquaternium-37 (and) paraffin liquidum (and) PPG-1 trideceth-6, polyquaternium 37 (and) propylene glycol dicaprate dicaprylate (and) PPG-1 trideceth-6, polyquaternium-7, polyquaternium 44th
  • Special shampoo formulations contain a) 0.0001 to 50% by weight or 0.001 to 10, or 0.005 to 1% by weight of at least one active ingredient according to the invention, b) 25 to 94.95% by weight of water, c) 5 to 50 % By weight of surfactants, c) 0 to 5% by weight of a further conditioning agent, d) 0 to 10% by weight of further cosmetic constituents.
  • Suitable anionic surfactants are, for example, alkyl sulfates, alkyl ether sulfates, alkyl sulfonates, alkylaryl sulfonates, alkyl succinates, alkyl sulfosuccinates, N-alkoyl sarcosinates, acyl taurates, acyl isothionates, alkyl phosphates, alkyl ether phosphates, alkyl ether carboxylates, Alpha-olefinsulfonates, especially the alkali and alkaline earth metal salts, e.g. As sodium, potassium, magnesium, calcium, and ammonium and triethanolamine salts.
  • the alkyl ether sulfates, alkyl ether phosphates and alkyl ether carboxylates can have between 1 to 10 ethylene oxide or propylene oxide units, preferably 1 to 3 ethylene oxide units, in the molecule.
  • Suitable examples are sodium lauryl sulfate, ammonium lauryl sulfate, sodium lauryl ether sulfate, ammonium lauryl ether sulfate, sodium lauroyl sarcosinate, sodium oleyl succinate,
  • Suitable amphoteric surfactants are, for example, alkylbetaines, alkylamidopropylbetaines, alkylsulfobetaines, alkylglycinates, alkylcarboxyglycinates, alkylamphoacetates or propionates, alkylamphodiacetates or dipropionates.
  • cocodimethylsulfopropyl betaine cocodimethylsulfopropyl betaine, lauryl betaine, cocamidopropyl betaine or sodium cocamphopropionate can be used.
  • Suitable nonionic surfactants are, for example, the reaction products of aliphatic alcohols or alkylphenols having 6 to 20 C atoms in the alkyl chain, which may be linear or branched, with ethylene oxide and / or propylene oxide.
  • the amount of alkylene oxide is about 6 to 60 moles per mole of alcohol.
  • alkylamine oxides, mono- or dialkylalkanolamides, fatty acid esters of polyethylene glycols, alkyl polyglycosides or sorbitan ether esters are also suitable.
  • the shampoo formulations may contain conventional cationic surfactants, such as. B. quaternary ammonium compounds, for example cetyltrimethylammonium chloride.
  • customary conditioning agents can be used in combination with the active compounds according to the invention to achieve certain effects.
  • cationic polymers with the name Polyquaternium according to INCI, in particular copolymers of vinylpyrrolidone / N-vinylimidazolium salts (Luviquat FC, Luviquat HM, Luviquat MS, Luviquat Care), copolymers of N-vinylpyrrolidone / dimethylaminoethyl methacrylate, quaternized with diethyl sulfate (Luviquat D PQ 1 1), copolymers of N-vinylcaprolactam / N-vinylpyrrolidone / N-vinylimidazolium salts (Luviquat D Hold), cationic cellulose derivatives (Polyquaternium-4 and -10), acrylamide copolymers (Polyquaternium-7).
  • silicone compounds for example polyalkylsiloxanes, polyarylsiloxanes, polyarylalkylsiloxanes, polyethersiloxanes or silicone resins.
  • suitable silicone compounds are dimethicone copolyols (CTFA) and amino-functional silicone compounds such as amodimethicones (CTFA).
  • CTFA dimethicone copolyols
  • ICI cationic guar derivatives
  • Oral care products according to the invention can be prepared in a manner known per se, e.g. be formulated as a toothpaste, tooth gel, or aqueous or aqueous-alcoholic oral care product (mouthwash).
  • Oral care compositions according to the invention contain, based on the weight of the composition, 0.00001 to 50% by weight, 0.0001 to 10% by weight, 0.001 to 5% by weight, 0.005 to 1% by weight or 0.1% to 20 wt .-%, 0.5 to 15 wt .-% or 1 to 5 wt .-% of the total amount of at least one active ingredient according to the invention
  • the oral care products in particular toothpastes, may also contain abrasives, such as silicon oxide hydrate, dicalcium phosphate dihydrate, calcium carbonate, sodium hydrogen carbonate, calcium pyrophosphate and aluminum oxide.
  • abrasives such as silicon oxide hydrate, dicalcium phosphate dihydrate, calcium carbonate, sodium hydrogen carbonate, calcium pyrophosphate and aluminum oxide.
  • a mixture of precipitated silica and chopped precipitated silica [Handbook of Pharmaceutical Excipients, The Pharmaceutical Society of Great Britain, 1 Lambeth High Street, London SE 17JN, England, pages 253-256] may also be used. The former is used because of its thixotropic properties, the second because of its better effectiveness in removing the substances adhering to the tooth surfaces.
  • the formulation of the oral care compositions of the invention may also contain suitable additives and vehicles to improve its properties and to facilitate its manufacture.
  • suitable additives and vehicles e.g. selected from binders, thickeners, fragrances, dyes, preservatives, wetting agents or humectants, surfactants, lubricants, opacifiers, remineralizers, surfactants, buffers, alcohols, vitamins, water, additional active ingredients and mixtures thereof.
  • any means normally used in the preparation of this type of formulations may be used, e.g. B. Tragantgummi.
  • the binder may be included in the formulation in an amount of 0.5-1.5% by weight of the total amount.
  • Oral thickening agents such as sodium carboxymethylcellulose, cellulose ethers, xanthan gum, carageenans, sodium alginate and carbopols may also be included in the oral care composition.
  • Inorganic thickeners such as silica thickeners, sodium aluminum silicates, and clays can also be used to provide the appropriate rheology.
  • the thickening agent may be included in the formulation in an amount of 0.5-5% by weight of the total amount.
  • the toothpaste can be prepared by adding a suitable customary fragrance, for.
  • a suitable customary fragrance for.
  • Essential oils including u.a. Clove oil, cinnamon oil, peppermint oil and spearmint oil are also suitable.
  • the perfume may be included in the formulation in an amount of 0.5-15% by weight of the total amount.
  • any of the dyes commonly used in the production of toothpaste can be used, for example, Brilliant Blue FCF, C.42090 [KIRSCH PHARMA].
  • the dye may be included in the formulation in an amount of 0.001-0.005% by weight of the total amount.
  • the preservative may be any conventional agent, such as a derivative of benzoic acid, e.g. B. p-hydroxy methyl benzoate act.
  • the preservative may be included in the formulation in an amount of 0.1-0.3% by weight of the total amount.
  • sweetener can be z. As sodium saccharin or cyclamic acid and derivatives thereof, for. As sodium cyclamate use.
  • the sweetener may be included in the formulation in an amount of 0.08-0.15% by weight of the total amount.
  • the wetting or wetting agent used to prevent the drying and hardening of the toothpaste is selected in particular from glycerol, sorbitol, propylene glycol, xylitol and liquid polyethylene glycols, in particular a mixture of sorbitol, glycerol and xylitol, eg in a proportion of 1-60 Wt .-% of the total amount.
  • a lubricant may be any of the commonly used in the formulation of a toothpaste agent, for. Dimethicone (polymer of dimethylpolysiloxane), which is a surface-active agent which helps to impart good rheological properties to the toothpaste of the present invention.
  • the lubricant may be included in the formulation in an amount of from 0.25% to 0.75% by weight of the total amount.
  • opacifiers any of the commonly used agents may be used, for. B. titanium dioxide.
  • the clouding agent may be contained in the formulation in an amount of 0.05 to 1% by weight of the total amount. As Reminaltechnischsmittel using a fluoride source, eg.
  • Sodium fluoride, stannous fluoride, and sodium monofluorophosphate by providing 100% of active fluoride as an agent for remineralizing the white lesions caused by the organic acids resulting from bacterial metabolism.
  • the remineralizing agent may be contained in the formulation in an amount of from 0.2 to 0.4% by weight of the total amount.
  • typical ingredients may be included, such as anionic surfactants, e.g. Sodium lauryl sulphate, sodium N-lauryl sarcosinate, sodium lauryl sulphoacetate and sodium alkyl glyceryl ether sulphonate.
  • anionic surfactants e.g. Sodium lauryl sulphate, sodium N-lauryl sarcosinate, sodium lauryl sulphoacetate and sodium alkyl glyceryl ether sulphonate.
  • the surfactant may be included in the formulation in an amount of from 0.05% to 5% by weight of the total amount
  • the toothpaste proposed by the invention may also contain vitamin selected from the group consisting of vitamin A, vitamin B5, vitamin C and vitamin E and mixtures thereof.
  • each vitamin in the formulation may be contained in an amount of 0.1 to 5% by weight of the total amount.
  • vitamins can be used as such, in the form of provitamins or in the form of acceptable pharmaceutical salts.
  • Vitamin A which is usually used in the form of its palmitate salt, promotes epithelialization of the oral mucosa and protects the gums.
  • Vitamin B5 more precisely D-panthenol, has an analgesic, healing and anti-inflammatory action, protects the epithelial mucosa, promotes epithelialization of injuries and smoothes the scars; it is suitable for the treatment of injuries resulting from tooth extraction, gingivitis, stomatitis, pain after the insertion of dentures, ulcers, traumatic mucosal lesions, chronic and retrograde aphthae. Vitamin C regenerates the epithelium of the oral mucosa, promotes collagen synthesis and the immune system (inflammatory mechanism) and increases the ability of phagocytes to protect against bacteria.
  • the vitamin E which is normally used in the form of its acetate salt, has an analgesic and anti-inflammatory effect, protects the oral mucosa against the over-oxidation of fat as a result of the formation of free radicals and against environmental contaminants (ozone, cigarette smoke, etc.) and promotes healing of the injuries.
  • the invention provides a toothpaste which, in addition to the aforementioned properties, also has anti-inflammatory and analgesic properties which increase the protective capacity of the membranes of the oral mucosa and reduce the plaque and tartar formation index as well as the bacterial contamination
  • Additional agents include antimicrobial and plaque-penetrating agents such as beta-naphthol, thymol, chlorothymol and hexylresorcinol; or germicidal compounds such as quaternary ammonium compounds; Tartar control agents such as tetrasodium pyrophosphate, GANTREZ polymer ® S-70, sodium tripolyphosphate, and zinc citrate; Peroxide compounds such as hydrogen peroxide and inorganic peroxides.
  • a buffer may also be used which is contained in concentrations suitable for maintaining a pH of about 6-8, such as alkali metal phosphate buffers.
  • concentrations suitable for maintaining a pH of about 6-8 such as alkali metal phosphate buffers.
  • the presence of potassium ions exerts an effect of alleviating the upper cerebral effect.
  • Water or alcohol may be contained in a proportion of 1 to 20% by weight of the total amount of the agent.
  • Glycol, sorbitol or propylene glycol may also be used in combination with the alcohol or instead of the alcohol.
  • the oral hygiene product of the present invention can be easily prepared by mixing appropriate amounts of the various ingredients in a e.g. be prepared with stirring blades equipped reactor.
  • the active ingredient content can be varied over a wide range, such as e.g. 0.00001 to 50 wt .-%, in particular 0.001 to 10 wt .-% or 0.005 to 1 wt .-% vary.
  • Patches according to the invention can be constructed in any desired manner, for example according to the matrix system, the membrane system or the nonwoven system (Drug Dev. Ind. Pharm. 14 (1988), 183-209; Drug Dev. Ind. Pharm. 13 (1987), 589- 651; Drugs of Today 23 (1987), 625-646.
  • the matrix system consists in the simplest way of 3 parts: the flexible support film, the active ingredient-containing adhesive matrix and a release liner. If a non-adhesive matrix is used, an edge zone of the backing film must be provided with adhesive to adhere to the skin.
  • a membrane system has at least 5 parts: a flexible support film, a reservoir with dissolved or suspended active substance, a membrane for controlling the release of active substance, an adhesive layer applied to the membrane and a release liner.
  • the layer containing the active ingredient is an absorbent nonwoven or porous polymer impregnated with a drug solution or suspension. This layer, which is firmly connected to the backing film, is covered by a release liner.
  • the edge of the support film is, for application to the skin, provided with adhesive. In principle, all active compounds according to the invention can be formulated in this way.
  • the adjuvants to be used are those customary for the production of plasters.
  • the adhesive agent usually a polymer having a glass transition temperature between -70 and -10, in particular -55 and -25 ° C, and a carrier film, which is coated with this adhesive agent, and the active ingredient are often emulsifiers, Thickening agents as well as substances intended to affect drug release and other adjuvants.
  • the tacky polymers having the above-mentioned low glass transition temperatures are known, for example, from US Pat. Nos. 2,973,282 and 3,307,544.
  • the self-adhesive tapes and films are said to stick to mere contact on the human skin, but the cohesion of the adhesive layer and its adhesion be greater than the adhesion to the skin on the carrier film, so that they can be removed almost without residue again.
  • copolymers based on acrylic and methacrylic acid esters of alcohols having 2 to 12, in particular 4 to 8, carbon atoms which may contain in copolymerized form numerous other comonomers, for example (meth) acrylic acid, (meth) acrylonitrile, (Meth ) acrylamide, N-tert-butyl (meth) acrylamide, vinyl esters such as vinyl acetate, propionate or butyrate, other vinyl compounds such as styrene, butadiene. Particularly noteworthy are butyl acrylate and 2-ethylhexyl acrylate.
  • the polymers can be crosslinked by adding small amounts of comonomer having 2 or more copolymerizable double bonds, ie, for example, diacrylates such as butanediol diacrylate, or divinyl compounds such as divinylbenzene, or by adding other crosslinking agents, for example melamine-formaldehyde resins.
  • comonomer having 2 or more copolymerizable double bonds ie, for example, diacrylates such as butanediol diacrylate, or divinyl compounds such as divinylbenzene
  • other crosslinking agents for example melamine-formaldehyde resins.
  • melamine-formaldehyde resins As sticky polymers it is further possible to use polyisobutylenes and polyvinyl ethers of different molecular weight.
  • the particle size of the dispersions should be between 50 and 500 nm, in particular between 50 and 200 nm.
  • Matrix patches can be prepared in a conventional manner by dissolving or finely dispersing the active ingredient in a suitable polymer solution and then extracting this active ingredient-containing self-adhesive composition to the film by means of a roll or knife coating method.
  • a suitable polymer solution e.g. polyethylene glycol
  • an organic solvent e.g. Ethanol or acetone
  • the patches can also be prepared according to the German patent application P 38 07 283.1 by incorporating the active ingredient in finely powdered form (particle size below 200, especially below 50 ⁇ ) in the aqueous latex dispersion, or dispersed or dissolved in an aqueous emulsifier and this mixture of aqueous latex dispersion at a temperature of 10 to 80, in particular 30 to 70 ° C admixed.
  • the salt of an active substance in aqueous solution can also be mixed with the polymer dispersion at a pH at which the active ingredient is present predominantly in the water-soluble ionized form. By pH shift, the active ingredient is then brought into the uncharged water-insoluble form and emulsified simultaneously into the dispersion.
  • the active ingredient is added, the emulsifier and water are added and the mixture is then mixed with the polymer dispersion.
  • the active substance-containing dispersion thus obtained is optionally provided with further auxiliaries and, as mentioned, drawn out in a manner known per se on a support film to form a film and dried.
  • the drying temperature may in this case be between room temperature and 100 ° C, with an optimum between desired rapid drying and avoidable blistering in the film and thermal stress of the active ingredient generally at 35 to 45 ° C.
  • the resulting films have thicknesses of 10 to 800, preferably 50 to 300 ⁇ .
  • the film production can be continuous or discontinuous.
  • the application process can be repeated several times until the film has reached the desired thickness.
  • the sticky polymer layer contains the active ingredient in a concentration in the range from 1 to 40, in particular 5 to 25 wt .-%. The same concentration also applies to the reservoir fluid at Membrane system and for the drug solution or dispersion, which is soaked in the nonwoven system, the fleece or the porous polymer.
  • Suitable emulsifiers for both the active compounds and the polymers are the surfactants customary therefor, such as the sodium salt of longer-chain fatty acids and the sulfuric monoester of an (optionally ethoxylated) fatty alcohol as examples of anionic surfactants and also polyoxethylated alkylphenols and longer-chain fatty alcohols (eg hexadecane- (1) -ol) and glycerol fatty acid partial esters as examples of nonionic surfactants and coemulsifiers.
  • the surfactants customary therefor such as the sodium salt of longer-chain fatty acids and the sulfuric monoester of an (optionally ethoxylated) fatty alcohol as examples of anionic surfactants and also polyoxethylated alkylphenols and longer-chain fatty alcohols (eg hexadecane- (1) -ol) and glycerol fatty acid partial esters as examples of nonionic surfactants and coe
  • the desired viscosity of the mass to be extruded may be e.g. be adjusted with polyacrylic acids or cellulose derivatives.
  • crosslinking agents which enhance the cohesion and thus the adhesive properties of the films, e.g. Melamine-formaldehyde resins are used.
  • cellulose derivatives or polyacrylates act as the film can absorb more water and thus the diffusion resistance decreases.
  • the release of the active ingredients can be further improved by the addition of hydrophilic plasticizers such as glycerol, 1, 2-propanediol of polyethylene glycols and lipophilic plasticizers such as triacetin, dibutyl phthalate or isopropyl myristate.
  • Matrix patches usually give a first-order drug release.
  • the support film to which the active substance-containing self-adhesive composition is dried is expediently impermeable to both the active substance and water vapor. It can e.g. of an aluminum-plastic composite foil, a metallised plastic foil, a plastic foil which faces the active-substance side with a barrier layer of e.g. Polyvinylidene chloride, or from a simple plastic film, e.g. Polyester film, consist.
  • the patches according to the invention which are constructed according to the membrane system, are likewise produced in a customary manner (for example EP 0 186 071 A2, US Pat. No. 4,262,003).
  • the patches constructed according to the nonwoven system are produced by bonding nonwovens or porous polymers fastened to the support film with a solution or dispersion of the active substance.
  • Stoffes be soaked in a hydrophilic or lipophilic solvent or solvent mixture. Subsequently, the impermeable release film is applied.
  • Cooling foods according to the invention can be in solid, liquid, semi-solid, pasty, creamy or foamed form (at ambient temperature).
  • they contain at least one effective (i.e., cooling) amount of at least one active ingredient of the invention.
  • Typical ingredients are fats, carbohydrates, proteins, fiber, water, alcohol and the like.
  • the protein portion may e.g. 0 to 50 wt .-%, based on the total weight of the food amount;
  • the fat content may e.g. from 0 to 50% by weight, based on the total weight of the food;
  • the carbohydrate portion may e.g. 0 to 90 wt .-%, based on the total weight of the food amount;
  • the fiber content may e.g. 0 to 90 wt .-%, based on the total weight of the food amount;
  • the proportion of water may e.g. 0 to 95 wt .-%, based on the total weight of the food amount;
  • the alcohol content may e.g. 0 to 15 wt .-%, based on the total weight of the food amount;
  • the proportion of active compounds according to the invention can e.g. in the range of 0.0001 to 50, 0.001 to 20, 0.005 to 1, or 0.01 to 10, in particular 0, 1 to 10 or 1 to 5 wt .-%, based on the total weight of the food.
  • carbohydrates are e.g. Mono- and disaccharides, glucose, galactose, mannose, lactose, maltose, and sucrose; Fructose and mannose; Polysaccharides such.
  • dietary fiber refers to soluble, insoluble, fermentable, non-fermentable or any combination of such dietary fiber.
  • dietary fiber may include soya fiber, pectin, certain resistant starches, oligofructose, inuline, oat fiber, pea fiber, Guar gum, gum acazia, modified cellulose act.
  • the fat ingredient may be any lipid or fat known to be suitable for use in nutrients.
  • Typical fats include milk fat, thistle oil, canola oil, egg yolk lipid, olive oil, cottonseed oil, coconut oil, palm oil, palm kernel oil, soybean oil, sunflower oil, fish oil and fractions of all the above oils derived therefrom, such as palm olein, medium chain triglycerides (MCT), and fatty acid esters, wherein the fatty acids z.
  • oils such as palm olein, medium chain triglycerides (MCT), and fatty acid esters, wherein the fatty acids z.
  • MCT medium chain triglycerides
  • fatty acid esters wherein the fatty acids z.
  • These are, for example, arachidonic acid, linoleic acid, palmitic acid, stearic acid, docosahexaenoic acid, eicosapentaenoic acid, linolenic acid, oleic acid, lauric acid, capric acid, caprylic acid, caproic
  • the protein can be any protein and / or amino acid mixture known to be suitable for use in nutrients.
  • Typical proteins are animal proteins, vegetable proteins such as soy protein, milk protein such as skimmed milk protein, whey protein and casein, and amino acids (or salts thereof) such as isoleucine, phenylalanine, leucine, lysine, methionine, threonine, tryptophan, arginine, glutamine, taurine, valine ,
  • Preferred protein sources are whey protein, sodium caseinate or calcium caseinate, which is optionally mixed with amino acids.
  • a preferred source of protein is hydrolyzed protein (protein hydrolyzate), optionally with amino acids added.
  • the protein hydrolyzate may be any suitable protein hydrolyzate used in a nutrient such as soy protein hydrolyzate, casein hydrolyzate, whey protein hydrolyzate, other animal and vegetable protein hydrolysates, and mixtures thereof.
  • the protein hydrolyzate of the composition of the invention is preferably a soy protein, whey protein or casein protein hydrolyzate comprising short peptides and amino acids and optionally added with additional amino acids.
  • the protein hydrolyzate suitable according to the invention contains a high proportion of free amino acids (eg more than 40%) and low molecular weight peptide fragments.
  • the hydrolyzed protein of the composition of the invention is also preferably added with various free amino acids to provide a nutritionally balanced amino acid content.
  • free amino acids include L-tryptophan, L-methionine, L-cystine, L-tyrosine and L-arginine.
  • the nutrients according to the invention optionally also contain vitamins and minerals. It will be understood by those skilled in the art that minimal requirements have been established for certain vitamins and minerals necessary for normal physiological function. The person skilled in the art also knows that the nutrients are given adequate additional amounts of vitamin and mineral components must be added to compensate for certain losses in the processing and storage of such compositions.
  • the inventive composition optionally contains nutritionally significant amounts of vitamins and minerals.
  • Examples of minerals, vitamins and other nutrients which are optionally present in the composition according to the invention include vitamin A, vitamin B 6 , vitamin B 12 , vitamin E, vitamin K, vitamin C, vitamin D, inositol, taurine, folic acid, thiamine , Riboflavin, niacin, biotin, pantothenic acid, choline, calcium, phosphorus, iodine, iron, magnesium, copper, zinc, manganese, chloride, potassium, sodium, beta-carotene, nucleotides, selenium, chromium, molybdenum and L-carnitine. Minerals are usually added in salt form.
  • the composition according to the invention also usually comprises emulsifiers and / or stabilizers such as lecithin (for example from egg or soya), modified lecithin (for example enzymatically or acetylated), carrageenan, xanthan gum, mono- and diglycerides, guar gum, Carboxymethylcellulose, stearoyl lactylates, succinylated monoglycerides, sucrose esters of fatty acids, diacetyl tartaric acid esters of monoglycerides, polyglycerol esters of fatty acids, or any mixtures thereof.
  • the composition of the invention optionally contains one or more natural or artificial flavor carriers to improve palatability.
  • any flavor carrier used in the sector such as strawberry, cherry, chocolate, orange, coconut, vanilla; Spices such as nutmeg and cinnamon; or citric acid.
  • the ingredient contributes to the overall nutritional profile of the composition, i. H. it contributes to the quality and quantity of the fat, protein and / or carbohydrate ingredient.
  • composition of the invention optionally also contains various other ingredients which may contribute to the nutritional value profile of the composition and / or impart desirable taste properties such as flavor enhancement or mouthfeel.
  • ingredients include peanuts, raisins, cheese powder, vinegar, salt, sodium bicarbonate.
  • the composition is usually provided with a chocolate or a flavored coating (eg, chocolate, vanilla, strawberry, etc.).
  • the composition of the invention also contains natural or artificial colors to enhance the aesthetic appeal.
  • the compositions of the invention may be in several physical forms, e.g. As liquid enteral nutrients or adult or child drinks, in a semi-solid form such as pudding, cream, mousse, or a solid form such as a nutrient bar or biscuit.
  • composition of the present invention may be prepared by known standard food processing techniques, for example by analogous methods to those described in the following references: U.S. Patents 4,670,268; 4,497,800; 4,900,566; 5, 104, 677; 5,389,395; and 5,223,285; Chocolate, Cocoa and Confectionery: Science and Technology, 3rd Ed., Bernard W. Minifie, Van Nostrand Reinhold, New York, 1989, pp. 502-506; to which full content is referred.
  • composition of the invention may be sterilized by known methods, for example, by heat treatment such as autoclaving or sterilizing or irradiation, or manufactured and packaged by sterile methods.
  • the composition of the invention may be packaged in any type of container or package known to be suitable for storing food, such as paper, glass, coated cardboard, plastic or coated metal cans.
  • composition of the invention may be nutritionally balanced.
  • nutritionally balanced is understood to mean that the composition contains adequate nutrients to maintain a healthy human life over extended periods of time.
  • the active ingredient content can be over a wide range, e.g. 0.00001 to 50 wt .-%, in particular 0.001 to 10 wt .-% or 0.005 to 1 wt .-% vary.
  • the equipment of textiles with cooling-acting compounds finds particular use where garments can come into direct contact with the skin, so that the active substance can exert its effects, for example locally or systemically, by transdermal transfer.
  • textiles were reported that are equipped with so-called wellness additives, ie substances that promote well-being (R. Breier "Megatrend Wellness - innovative Ideas for Textile Equipment", 31st Aachen Textile Days November 2004).
  • Insecticidal equipment is desirable in terms of material protection, e.g. Equipment of the textile against moths, etc., but especially for the defense against parasitic insects, such as mosquitoes, of interest.
  • the fundamental problem in the finishing of textiles with active ingredients is the binding of the active ingredient to the textile carrier, which on the one hand must ensure the permanence of the equipment and on the other hand must be chosen so that the active ingredient does not lose its effect.
  • various approaches are proposed in the prior art. For example, Cyclodextrins for the attachment of active ingredients to textiles proposed (see, for example, DE-A-19810951 and EP-A-0 392 608).
  • Cyclodextrins are cyclic oligosaccharides formed by enzymatic degradation of starch.
  • the most common cyclodextrins are a-, ß- and ⁇ -cyclodextrins, which consist of six, seven or eight a-1, 4-linked glucose units.
  • a characteristic feature of the cyclodextrin molecules is their ring structure with largely invariable dimensions. The inner diameter of the rings is about 570 pm for ⁇ -cyclodextrin, about 780 pm for ⁇ -cyclodextrin and about 950 ⁇ m for ⁇ -cyclodextrin. Due to their structure, cyclodextrins are able to trap guest molecules, in particular hydrophobic guest molecules, in varying amounts up to saturation.
  • EP-A-1710345 describes the finishing of textiles with fragrances and other low molecular weight organic actives via an amylose-containing substance having an amylose content of at least 30% bound to the textile. Due to the amylose content of the amylose-containing substance, the active substance is bound to the textile and released in a controlled manner, so that the effect is retained over a long period of time. It is assumed that the active substance is reversibly bound in the cavities formed by the helical conformation of the amylose in the sense of an inclusion compound, similar to cyclodextrins, which on the one hand achieves fixation of the active ingredient on the surface of the textile support and, on the other hand, controlled release is possible.
  • amylose-containing starches ie native starches, modified starches and starch derivatives, whose amylose content is at least 30% by weight and in particular at least 40% by weight
  • the starch may be native, for example corn starch, wheat starch, potato starch, sorghum starch, rice starch or marten starch, obtained by partial digestion of native starch or chemically modified.
  • pure amylose as such, for example enzymatically obtained amylose, for. B. from sucrose won amylose.
  • mixtures of amylose and starch are also suitable, provided that the total content of amylose is at least 30% by weight, based on the total weight of the mixture. It is understood that here and below, all information in wt .-%, which relate to amylose or amylose-containing substances, in mixtures of amylose and starch are always based on the total weight of amylose + starch, unless expressly stated otherwise.
  • amylose-containing substances in particular amylose and amylose-containing starches, and amylose / starch mixtures whose amylose content is at least 40% by weight and in particular at least 45% by weight, based on the total weight of the substance.
  • amylose content will not exceed 90% by weight and in particular 80% by weight.
  • amylose-containing starches are sold by the companies Cerestar under the trademark Amylogel® and National Starch under the trade names HYLON® V and VII.
  • the textile containing the amylose-containing substance can generally be present in an amount of at least 0.5% by weight, preferably at least 1% by weight, and in particular at least 2 wt .-%, each based on the weight of the textile, equip.
  • the amylose-containing substance in an amount of not more than 25 wt .-%, often not more than 20 wt .-% and in particular not more than 15 wt .-%, based on the weight of the textile, use to not to adversely affect the tactile properties of the textile.
  • the textile material is equipped with the amylose-containing substance as such and then treated the textile thus treated with a suitable treatment of the active ingredient.
  • the amylose-containing substance present on the textile material is loaded with the active substance.
  • amylose-containing substance together with an active ingredient to equip the textile.
  • the active ingredient and the amylose-containing substance be applied both as a mixture of separate components and in the already preformed form of the amylose-drug complex.
  • the active ingredient in an amount that is sufficient for the desired effect.
  • the upper limit is determined by the maximum uptake capacity of the amylose units of the amylose-containing substance used and will generally not exceed 20% by weight and frequently 10% by weight, based on the amylose content of the substance.
  • the active compound is usually added in an amount of 0.00001 to 15 wt .-%, 0.0001 to 10 wt .-%, 0.001 to 5 wt .-%, 0.005 to 1 wt .-% or 0.1 to 10 wt .-% or 0.5 to 5 wt .-%, based on the amylose content of the amylose-containing substance.
  • active compounds according to the invention are suitable as further active ingredients. Mention may be made of those active substances which, as is known, can form inclusion compounds with cyclodextrins. Particularly suitable are active compounds which have hydrocarbon groups and in particular aliphatic, cycloaliphatic and / or aromatic structures. The molecular weight of the drugs is typically below 1000 daltons, and often in the range of 100 to 600 daltons.
  • inorganic compounds such as hydrogen peroxide, which can be known to be bound in cyclodextrins (see F. Vögtle, Supramolecular Chemistry, 2nd edition, B.G. Teubner, Stuttgart 1992, cyclodextrins and literature cited therein)
  • the other active ingredients include, in particular, pharmaceutical active ingredients and active ingredients which promote the well-being of living beings, in particular of humans and which are commonly referred to as "wellness additives".
  • the wellness additives do not necessarily have a therapeutic effect. Rather, the well-being promoting effect can be based on a variety of factors such as nourishing, stimulating, cosmetic or other effects. Equally suitable are organic agents that act against parasitic organisms.
  • active substances which act against fungi and / or microorganisms, for example fungicides and bactericides, or which act against animal pests such as snails, worms, mites, insects and / or rodents, for example nematicides, molluscicides, insecticides, acaricides, rodenticides and repellents
  • active ingredients as well as further active agents against weeds, ie herbicides, or perfumes.
  • Preferred active pharmaceutical ingredients are those that are known to be absorbed through the skin.
  • ibuprofen include, for example, ibuprofen, flurbiprofen, acetylsalicylic acid, acetamidophen, apomorphine, butylated hydroxytoluene, chamulenes, gujaculas, chlorthalidone, cholecalciferol, dicumarol, digoxin, diphenylhydantoin, furosemide, hydroflumethiazide, indomethacin, ipronocidyl phosphate, nitroglycerin, nicotine, nicotinic acid amide, oubain, oxprenolol, Papaverine alkaloids such as papaverine, laudanosine, ethaverine and narcotin, as well as berberine, Retionol, trans-retinoic acid, pretinol, spironolactone, sulpiride, theophylline, theobromine,
  • active substances which are suitable according to the invention and have an action against parasitic organisms are the nematicides, bactericides, fungicides mentioned under www.reith-pfister.de/www.list.html and www.hclrss.demon.co.uk/class pesticides.html. Insecticides, insect repellents, acaricides and molluscicides.
  • bactericidal and fungicidal substances include:
  • Antibiotics e.g. Cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxin, streptomycin, penicillin or gentamycin;
  • Organic compounds and complexes of biocidal metals eg complexes of silver, copper, tin and / or zinc such as bis (tributyltin) oxide, copper, zinc and tin naphthenates, oxine copper such as Cu-8, Tris-N- ( cyclohexyldiazeniumdioxy) -aluminum, N- (cyclohexyldiazeniumdioxy) -tributyltin, bis-N- (cyclohexyldiazeniumdioxy) -copper; Quaternary ammonium salts, for example benzyl C 8 -C 18 -alkyldimethylammonium halides, in particular chlorides (benzalkonium chlorides);
  • aliphatic nitrogen fungicides and bactericides such as cymoxanil, dodin, dodicin, guazidines, iminoctadine, dodemorph, fenpropimorph, fenpropidine, tridemorph, substances having peroxide groups such as hydrogen peroxide, and organic peroxides such as dibenzoyl peroxide;
  • Triazole fungicides such as azaconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, epoxiconazo, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, metconazole, propiconazole, tetraconazole, tebuconazole and triticonazole; Strobilurins such as dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin Sulfonamides such as tolylfluanid and diclofluanid;
  • iodine compounds such as diiodomethyl-p-tolylsulfone, napcocide, 3-iodo-2-propynyl alcohol, 4-chlorophenyl-3-iodopropargylformal, 3-bromo-2,3-diiodo-3-propenylethylcarbonate, 2,3,3-triiodoallylalcohol, 3-iodo 2-propynyl-n-hexyl carbamate, 3-bromo-2,3-diiodo-2-propenyl alcohol, 3-iodo-2-propynylphenyl carbamate, 3-iodo-2-propynyl-n-butyl carbamate, O-
  • Isothiazolinones such as N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4,5-dichloro-N-octylisothiazolin-3-one, 1,2-benzisothiazol-3 (2H) one, 4, 5-trimethylisothiazol-3-one and N-octylisothiazolin-3-one.
  • Organophosphates such as acephates, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyriphos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoates, disulphoton, ethion, fenitrothion, fenthion, isoxathione, malathion, methamidophos, methidathion, methyl parathion, mevinphos, monocrotophos, Oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidone, phorates,
  • Phoxim pirimiphos-methyl, profenofos, prothiofos, sulprophos, triazophos, trichlorfon; especially pyrethroids such as acrinatrine, allethrin, bioallethrin, barthrin, bifenthrin, bioethanomethrin, cyclethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, ⁇ -cypermethrin,
  • Pyrrole and pyrazole insecticides such as acetoprole, ethiprole, fipronil, tebufenpyrad, tolfenpyrad, chlorfenapyr and vaniliprole.
  • repellent active ingredients are in particular anthraquinone, acridine bases, copper naphthenate, butopyronoxyl, dibutyl phthalate, dimethyl phthalate, dimethyl carbate, ethohexadiol, hexamides, methoquine-butyl, N-methyl neodecanamide, camphor, bergamot oil, pyrethrum, clove oil, geranium oil, thyme oil and in particular diethyl m-toluamide and 1-piperidinecarboxylic acid 2- (2-hydroxyethyl) -1-methylpropyl ester (Picardin).
  • Examples of wellness additives are in particular the substances listed below and mixtures of substances, eg
  • Fats preferably of vegetable origin, e.g. lecithins,
  • Vegetable oils such as jojoba oil, tea tree oil, clove oil, evening primrose oil, almond oil, coconut oil, avocado oil, soybean oil and the like,
  • Fatty acids e.g. ⁇ -6 fatty acids, linolenic acid, linoleic acid,
  • Waxes of animal or plant origin such as beeswax, candelilla wax, shea butter, shore butter, mango seed butter, Japan wax and the like,
  • Vitamins in particular fat-soluble vitamins, eg. As tocopherols, vitamin E, vitamin A and the like,
  • Cortico-steroids such as cortisone, corticosterone, dexamethasone, triamcinolone, methylprednisolone, fludrocortisone, fluocortolone, prednisone, prednisolone, progesterone, amino acids, e.g. Arginine, methionine,
  • Plant extracts such as algae extract, horse chestnut extract, mango extract and the like.
  • Suitable binders are on the one hand film-forming, water-insoluble polymers and, on the other hand, low molecular weight reactive substances which polymerize with heating.
  • the binder will be used in an amount such that the weight ratio of amylose-containing substance to water-insoluble polymer is in the range of 1: 1 to 100: 1, preferably in the range of 1: 5: 1 to 50: 1 and especially in the range of 2: 1 to 20: 1.
  • the film-forming polymers are used in the form of an aqueous dispersion of finely divided polymer particles. The particle size is of secondary importance for the success of the invention.
  • the film-forming polymer may in particular have a glass transition temperature T G in the range from -40 to 100 ° C, preferably -30 to +60 ° C, in particular -20 to +40 ° C.
  • T G glass transition temperature
  • the glass transition temperature of the main component is in the range of -30 ° C to +60 ° C, and more preferably in the range of -20 ° C to +40 ° C.
  • all polymeric constituents have a glass transition temperature in these ranges.
  • the glass transition temperatures given here refer to those determined by DSC according to ASTM D 3418-82. te "midpoint temperature". In the case of crosslinkable binders, the glass transition temperature refers to the uncrosslinked state.
  • Suitable film-forming polymers are based on the following polymer classes:
  • acrylate resins pure acrylates: copolymers of alkyl acrylates and alkyl methacrylates
  • styrene acrylates copolymers of styrene and alkyl acrylates
  • polyvinyl esters especially polyvinyl acetates and copolymers of vinyl acetate with vinyl propionate
  • vinyl ester-olefin copolymers e.g. Vinyl acetate / ethylene copolymers
  • vinyl ester-acrylate copolymers e.g. Vinyl acetate / alkyl acrylate copolymers and vinyl acetate alkyl acrylate ethylene terpolymers
  • Aqueous polyurethane dispersions (1) which are suitable for the process according to the invention are in particular those which are used for the coating of textiles (see, for example, J. Hemmrich, Int. Text. Bull. 39, 1993, No. 2, p. 56; "Aqueous Polyurethane Coating Systems” Chemiefasern / Textilind. 39 91 (1989) T149, T150, W.
  • Aqueous polyurethane dispersions are commercially available, for. B. under the trade names Alberdingk® the Fa. Alberdingk, Impranil® the Fa. BAYER AG, Permutex® the Fa. Steel, Waalwijk, Netherlands, BASF SE or can be prepared by known methods, as described for example in "Preparation for Polyurethanes "in Houben-Weyl," Methods of Organic Chemistry ", Volume E 20 / Macromolecular Substances, p. 1587, D. Dietrich et al., Angew. Chem. 82 (1970), p. 53 et seq., Angew.
  • the film-forming polymers can be self-crosslinking, ie the polymers have functional groups (crosslinkable groups) which react when the composition is dried, if appropriate when heated, with one another, with the functional groups of the amylose or with a low-molecular crosslinking agent to form bonds.
  • crosslinkable functional groups include aliphatically bonded OH groups, NH-CH 2 -OH groups, carboxylate groups, anhydride groups, capped isocyanate groups and amino groups.
  • the proportion of reactive functional groups is from 0.1 to 3 mol / kg of polymer.
  • Crosslinking can be effected within the polymer by reaction of complementary reactive functional groups.
  • the crosslinking of the polymer is effected by addition of a crosslinker having reactive groups which are complementary in their reactivity with the functional groups of the crosslinker.
  • Suitable pairs of functional groups which have a complementary reactivity are known to the person skilled in the art. Examples of such pairs are OH / COOH, OH / NCO, NH 2 / COOH, NH 2 / NCO and M 2+ / COOH, where M 2+ is a divalent metal ion such as Zn 2+ , Ca 2+ , or Mg 2+ stands.
  • suitable crosslinkers are the di- or polyols mentioned below for the polyurethanes; primary or secondary diamines, preferably primary diamines, e.g. B.
  • alkylenediamines such as hexamethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, N, N-bis [(aminopropyl) amino] ethane, 3,6-dioxaoctanediamine, 3,7-dioxanonanediamine, 3,6,9-Trioxaundecandiamin or Jeffamine, (4 , 4 -
  • Diaminodicyclohexyl) methane (4,4'-diamino-3,3-dimethyldicyclohexyl) methane;
  • Amino alcohols such as ethanolamine, hydroxypropylamine; ethoxylated di- and oligoamines;
  • Dihydrazides of aliphatic or aromatic dicarboxylic acids such as adipic dihydrazide;
  • Dialdehydes such as glyoxal; partially or completely O-methylated melamines, and compounds or oligomers containing on average two or more, preferably three or more isocyanate groups or reversibly z.
  • the ratio of crosslinker to polymeric binder is such that the molar ratio of the reactive groups in the polymeric binder (total amount of reactive groups in the polymers) to the reactive groups in the crosslinker is usually in the range of 1:10 to 10: 1 and preferably in the range of 3: 1 to 1: 3.
  • the weight ratio of polymeric binder (calculated as solid) to crosslinker is in the range from 100: 1 to 1: 1 and in particular in the range from 50: 1 to 5: 1.
  • the amylose can be fixed to the amylose-containing substance with water-insoluble polymers or the amylose-containing substance also with reactive compounds which have at least one, relative to the OH groups of the amylose reactive group and at least one further functional group, compared to the functional groups on the fibers of the textile material, for example OH groups, NH 2 Groups or COOH groups, reactive, fix on the textile material.
  • reactive compounds which have at least one, relative to the OH groups of the amylose reactive group and at least one further functional group, compared to the functional groups on the fibers of the textile material, for example OH groups, NH 2 Groups or COOH groups, reactive, fix on the textile material.
  • the reactive compounds include the above-mentioned crosslinkers and the substances proposed in DE-A 40 35 378 for the fixation of cyclodextrins, for example N-hydroxymethyl and N-alkoxymethyl derivatives of urea or urea-type compounds such as dimethylolurea (bis (hydroxymethyl) urea), di (methoxymethyl) - urea, dimethylolalkanediol diurethanes such as ⁇ , ⁇ -dimethylolethyleneurea (N, N-bis (hydroxymethyl) imidazolin-2-one), ⁇ , ⁇ -dimethylol-dihydroxyethyleneurea (N, N-bis (hydroxymethyl) -4,5-dihydroxyimidazoline-2-one) on), dimethylolpropyleneurea and the like.
  • dimethylolurea bis (hydroxymethyl) urea
  • di (methoxymethyl) - urea dimethylolalkanediol diurethanes
  • Such materials are commercially available in the form of aqueous formulations for the finishing of textiles, for example under the trade names Fixapret® and Fixapret®-eco from BASF SE.
  • the reactive materials that can be used to fix the amylose-containing substance on the textile material include in particular compounds having 2, 3, 4 or more (optionally reversibly blocked) isocyanate groups, especially those with bisulfite or CH-acidic compounds or Oximene, for example butanone oxime reversibly blocked polyisocyanate prepolymers based on polyether and polyester urethanes, which are described in DE 2837851, DE 19919816 and the older European Patent Application 03015121.
  • Such products are also commercially available, for example under the trade names PROTOLAN®367 and PROTOLAN®357 of Rotta GmbH, Mannheim.
  • the procedure known for the fixation of cyclodextrins can also be used in an analogous manner in which the cyclodextrin or, in the present case, the amylose-containing substance is provided with reactive anchors, for example by mixing with dicarboxylic acids or dicarboxylic acid anhydrides, such as maleic acid or fumaric acid , Maleic anhydride, succinic acid, succinic anhydride or adipic acid, with diisocyanates, e.g.
  • Reactive anchors can also be produced on the amylose-containing substance by reaction with 1,3,5-trichlorotriazine, 2,3-dichloroquinoxaline-5,6-carboxylic acid chloride and with chlorodifluoropyrimidine.
  • alkyoxysilanes such as diethoxydimethylsilane, dimethoxydimethylsilane, triethoxyphenylsilane, tetraethoxysilane and dimeric, trimeric and higher condensation products of these compounds can also be used to fix the amylose.
  • Textile materials here and below include woven, knitted, knitted and nonwoven fabrics.
  • the textile materials can be constructed from natural fiber yarns, synthetic fiber yarns and / or blended yarns.
  • all fiber materials commonly used for the production of textiles come into consideration as fiber materials. These include cotton, wool, hemp fiber, sisal fibers, flax, ramie, Polyacrylonitrile fibers, polyester fibers, polyamide fibers, viscose fibers, silk, acetate fibers, triacetate fibers, aramid fibers, and the like, and mixtures of these fiber materials.
  • the finishing of the textile materials with the amylose-containing substance can be carried out in a manner known per se, e.g. by means of the process described in DE-A 4035378 for the equipment of textiles with cyclodextrins.
  • amylose-containing substance optionally as a complex with the active substance, is already incorporated into the fiber, the filament and / or the yarn from which the fabric is made.
  • the textile material will be treated before or after fabrication with the amylose-containing substance or a complex of amylose-containing substance and active ingredient.
  • the textile will be treated with an aqueous liquor which contains the amylose-containing substance and, if appropriate, the active ingredient in sufficient quantity.
  • the concentration of amylose-containing substance in the liquor is in the range from 1 to 40% by weight, in particular in the range from 2 to 20% by weight. and especially in the range of 4 to 15% by weight.
  • the type of treatment is of minor importance and may be described, for example, as a minimum order, e.g. by spray application, as a normal job in the padder or as a high-moisture application.
  • the textile material is impregnated with the aqueous liquor.
  • a liquor is to be prepared with water, in which the desired amount of amylose-containing substance and optionally active ingredient is contained, e.g. 0.5 to 20% by weight (based on the weight of the textile to be finished).
  • the textile material is left over a period of time, e.g. Soaked with the treatment liquor for 10-60 minutes in equipment sets suitable for this purpose (for example reel skid, roller skid, paddle, etc.) and then squeezed and / or spun off as indicated above.
  • the liquor ratio here is usually in the range from 1: 2 to 1:50 and in particular in the range from 1: 3 to 1:20.
  • Such methods are known in the art, for example from HK Rouette, Lexikon the Textilveredlung, Laumann-Verlag, Dülmen 1995, p 669 ff.
  • the treatment with the liquor is followed by a drying process.
  • the temperatures are usually in the range of 100 to 200 ° C and preferably in the range of 120 to 180 ° C.
  • the drying can be carried out in the devices customary for this purpose, in the case of ready-made goods, for example by dry-bluing at the temperatures indicated above.
  • the textile material will usually be guided over one or more tenter frames following the order.
  • the drying leads to a fixation of the amylose-containing substance on the textile fibers.
  • the drying temperature will not fall below 100 and is preferably in the range of 120 to 200 ° C and in particular in the range of 140 to 180 ° C. In general, the drying is carried out for a period of 1 to 10 minutes, in particular 1 to 2 minutes, longer drying times are also suitable.
  • the aqueous liquor contains, in addition to the amylose-containing substance and optionally the active ingredient, at least one surface-active substance (or surfactant) which is used to disperse the amylose-containing substance and the active ingredient in the aqueous Fleet is suitable.
  • the surfactant is an oligomeric or polymeric dispersant.
  • oligomeric or polymeric dispersant unlike low molecular weight surfactants, includes those dispersants whose number average molecular weight is typically at least 2000 daltons, e.g. 2000 to about 100,000 daltons and in particular in the range of about 3000 to 70,000 daltons.
  • the aqueous liquor contains the polymeric or oligomeric dispersant in an amount of 0.5 to 20 wt .-%, preferably 1 to 18 wt .-% and in particular 5 to 15 wt .-%, based on the amylose-containing substance.
  • Suitable oligomeric or polymeric dispersants are water-soluble and include both neutral and amphoteric water-soluble polymers and cationic and anionic polymers, the latter being preferred.
  • neutral polymeric dispersants are polyethylene oxide, ethylene oxide / propylene oxide copolymers, preferably block copolymers, polyvinylpyrrolidone and copolymers of vinyl acetate with vinylpyrrolidone.
  • the preferred anionic oligomeric or polymeric dispersants are characterized in that they have carboxyl groups and / or sulfonic acid groups and are usually used as salts, for example as alkali metal salts or ammonium salts.
  • Preferred anionic dispersants are, for example, carboxylated derivatives of cellulose such as carboxymethylcellulose, homopolymers of ethylenically unsaturated C 3 -C 8 -mono- and C 4 -C 8 -dicarboxylic acids, for example acrylic acid, methacrylic acid, maleic acid, itaconic acid, copolymers of at least two different ethylenic unsaturated C 3 -C 8 monocarboxylic and C 4 - C 8 dicarboxylic acids as mentioned above, and copolymers of at least one of the abovementioned ethylenically unsaturated C 3 -C 8 mono- or C 4 -C 8 dicarboxylic acid with at least one neutral comonomers.
  • carboxylated derivatives of cellulose such as carboxymethylcellulose
  • neutral comonomers examples include N-vinyllactams such as N-vinylpyrrolidone, vinyl esters of aliphatic C 2 -C 16 -carboxylic acids such as vinyl acetate, vinyl propionate, amides of the aforementioned ethylenically unsaturated carboxylic acids such as acrylamide, methacrylamide and the like, hydroxy-C 1 -C 4 -alkyl (meth) acrylates such as hydroxyethyl acrylate and methacrylate, esters of ethylenically unsaturated C 3 -C 8 mono- or C 4 -C 8 dicarboxylic acids with polyethers, for example esters of acrylic acid or methacrylic acid with polyethylene oxides or ethylene oxide / propylene oxide block copolymers, vinylaromatics such as Styrene and C 2 -C 16 olefins such as ethylene, propene, 1-hexene, 1-octene,
  • homopolymers of ethylenically unsaturated sulfonic acids such as styrenesulfonic acid and acrylamidopropanesulfonic acid and their copolymer with the abovementioned comonomers.
  • the proportion of the ethylenically unsaturated acid will generally be at least 20% by weight and not exceed a value of 90% by weight and in particular 80% by weight, based in each case on the total weight of all monomers constituting the polymer ,
  • Copolymers of at least one of the abovementioned acids and at least one comonomer are known for this purpose and are available commercially, for example the copolymers of acrylic acid and maleic acid as Sokalan grades from BASF AG.
  • preferred anionic dispersants are phenolsulfonic acid-formaldehyde condensates and naphthalenesulfonic acid-formaldehyde condensates (e.g., the Tamol and Setamol brands of BASF) and lignosulfonates.
  • Useful dispersants are also low molecular weight anionic, nonionic, cationic, ampholytic and zwitterionic surfactants.
  • Suitable surfactants are, for example, the alkali metal, ammonium or amine salts of C 8 -C 18 -alkyl sulfates, such as sodium lauryl sulfate; C 8 -C 18 alkyl sulfonates, such as dodecyl sulfonate; C 8 -C 18 alkyl ether sulfates; and C 8 -C 18 - ethoxylates; polysorbate; C 8 -C 18 alkyl glycinates; C 8 -C 18 -
  • alkyldimethylamine a compound that has a higher degree of branching properties
  • Betaines etc. Preferred are the alkyl sulfates and alkyl sulfonates.
  • the textile can be treated with the polymer in a separate working step.
  • the treatment is carried out together with the amylose-containing substance.
  • a particular embodiment relates to a process wherein the aqueous liquor additionally comprises a dispersed, film-forming, water-insoluble polymer of the type referred to above.
  • the amount of film-forming polymer is chosen so that the weight ratio of amylose-containing substance to water-insoluble polymer in the range of 1: 1 to 100: 1, preferably in the range of 1, 5: 1 to 50: 1 and in particular in the range of 2: 1 to 20: 1.
  • the equipment of the textile with the active ingredient may be made in a separate operation or in one operation together with the equipment containing the amylose-containing substance.
  • the active compound which is usually insoluble in water, is emulsified or dispersed in water, if appropriate using suitable surface-active substances.
  • Suitable surfactants are, in particular, the aforementioned low molecular weight surfactants, and among these preferably the nonionic surfactants, particularly polyoxyethylene sorbitan esters, esters of mono- or oligosaccharides with C 6 -C 18 - fatty acids and particularly preferably C8-C18 alkyl ethoxylates, especially those having a degree of ethoxylation in the range from 6 to 50.
  • the aqueous liquor contains the active ingredient in an amount of 0, 1 to 10 wt .-% and in particular in an amount of 0.2 to 5 wt .-%.
  • the amount of surface-active substance is usually in the range of 0.5 to 50 wt .-% and in particular in the range of 3 to 30 wt .-%, based on the active ingredient.
  • the application of the active ingredient from aqueous liquor can be carried out by the methods customary for this purpose, for example by means of a padder.
  • the equipment can also carry out the equipment with active ingredient and amylose-containing substance in one operation.
  • the aqueous liquor of the amylose-containing substance now additionally containing the at least one active substance.
  • the active ingredient can be added separately to the liquor or in the form of an inclusion compound, ie in the form of a host-guest complex with the amylose-containing substance.
  • the process of the present invention can be used to finish any type of fabric including fabrics, knits, nonwovens, and the like. The type of textile material depends primarily on the desired application.
  • the textiles to be finished can be ready-made products such as clothing, including underwear and outerwear, such as shirts, trousers, jackets, outdoor, trekking and military equipment, roofs, tents, nets, eg insect screens and curtains, hand and hand towels Bath towels, bed linen and the like act.
  • the equipment can be made on the raw material in bale or roll form.
  • the textiles treated with active substances against parasitic organisms are, in addition to the protection of humans, also particularly suitable for animal protection for protection against ticks, mites, fleas and the like.
  • the textile materials may be composed of natural fiber yarns, synthetic fiber yarns and / or blended yarns, wherein the fabrics usually have a basis weight in the range of 10 to 500 g / m 2, preferably 20 to 250 g / m 2 .
  • fiber materials include cotton, wool, hemp fiber, sisal fibers, flax, ramie, polyacrylonitrile fibers, polyester fibers, polyamide fibers, viscose fibers, silk, acetate fibers, triacetate fibers, aramid fibers and the like, and mixtures of these fiber materials.
  • glass fibers and mixtures of the aforementioned fiber materials with glass fibers z For example, fiberglass / kevlar blends.
  • the active ingredients remain even after several washes in the textiles equipped with it.
  • the so-equipped textiles are characterized by a pleasant feel, which is particularly advantageous for the comfort of wearing made of these textiles clothing.
  • the active ingredient content can be over a wide range, e.g. 0.00001 to 50 wt .-%, in particular 0.001 to 10 wt .-% or 0.005 to 1 wt .-% vary.
  • the active compounds according to the invention can also be advantageously used for the production of tobacco products.
  • tobacco products include cigars, cigarettes, pipe tobacco, chewing tobacco, and snuff.
  • the production of tobacco products supplemented with cooling additives is known per se and is described, for example, in US Pat. Nos. 1,111,127, 5,752,529 and US 2005/0000529, to which reference is hereby expressly made.
  • the active compounds according to the invention are also advantageously suitable for the production of packaging materials.
  • the preparation is also carried out in a conventional manner.
  • the active ingredients may be incorporated into the packaging material, in free or e.g. encapsulated form, incorporated or applied to the packaging material, in free or encapsulated form.
  • suitably finished plastic packaging materials can be prepared as described in the literature for the preparation of polymer films (e.g., Ullmann, 6th Edn, 2003. Vol. 36, p. 567).
  • the preparation of appropriately coated papers is also known and e.g. described in Ullmann, Vol. 25, p. 106 ff, 6th Edn, 2003. 5.
  • the compounds according to the invention (cooling agents) of the structural types 1, 2 and 3 can be combined with further known active compounds, in particular also those with comparable action.
  • they may be fertilized with known refrigerating compounds, such as e.g. Menthol, menthone, N-ethyl-p-menthane carboxamide (WS-3, also called menthan-3-carboxylic acid N-ethylamide), N-2,3-trimethyl-2-isopropylbutanamide (WS-23), menthyl lactate (Frescolat® ML), menthone glycerol acetal (Frescolat® MGA), mono-menthyl succinate (Physcool®), mono-menthyl glutarate, O-menthyl-glycerol, menthyl-N, N-dimethyl succinamate.
  • refrigerating compounds such as e.g. Menthol, menthone, N-ethyl-p-menthane carboxamide (
  • the cooling active compounds according to the invention may preferably be combined with the following cooling active ingredients: menthol and menthol derivatives (eg L-menthol, D-menthol, racemic menthol, isomenthol, neoisomenthol, neomenthol) menthyl ether (eg (l Menthoxy) -1,2-propanediol, (1-menthoxy) -2-methyl-1,2-propanediol, 1-menthyl methyl ether), menthyl ester (eg menthyl formate, menthyl acetate, menthyl isobutyrate, menthyl lactate, L-menthyl-L) Lactate, L-menthyl D-lactate, menthyl (2-methoxy) acetate, menthyl (2-methoxyethoxy) acetate, menthyl pyroglutamate), menthyl carbonates (eg
  • a dicarboxylic acid or its derivatives eg mono-menthyl succinate, mono-menthyl glutarate, mono-menthyl malonate
  • the cooling active compounds according to the invention can particularly preferably be combined with the following cooling active ingredients: menthyl ether (eg (1-menthoxy) -1,2-propanediol, (1-menthoxy) -2-methyl-1 , 2-propanediol), more polar menthyl esters (eg, menthyl lactate, L-menthyl-L-lactate, L-menthyl D-lactate, menthyl (2-methoxy) acetate, menthyl (2-methoxyethoxy) acetate, menthyl pyroglutamate), menthyl carbonates (eg
  • Menthyl propylene glycol carbonate, menthyl ethylene glycol carbonate, menthyl glycerol carbonate), the half-esters of menthol with a dicarboxylic acid or its derivatives eg, mono-menthyl succinate, mono-menthyl glutarate, mono-menthyl malonate, O-menthyl succinate N, N- (dimethyl) amide, O-menthyl succinic ester amide
  • Menthanecarboxamides according to the invention eg menthane carboxylic acid N-ethylamide [WS3], No (menthane carbonyl) glycine ethyl ester [WS5], menthane carboxylic acid N- (4-cyanophenyl) amide, menthane carboxylic acid N- (alkoxyalkyl) amides), menthone derivatives (eg L-menthone glycerol ketal) , 2,3-di
  • the specific part of the invention relates to the use of very specific compounds (TRPM8 receptor modulators) for producing a long-lasting physiological cooling effect on the skin or mucosa.
  • the specific part of the invention further relates to mixtures and preparations (compositions) comprising specific such compounds. It also relates to a process for the preparation of a medicament as well as a process for achieving a physiological cooling effect on the skin and / or mucous membranes, wherein in each case particularly suitable compounds are used.
  • Physiological cooling agents are regularly used to produce a cool sensory impression on the skin or mucosa, for example on the mucosa in the mouth, nose and / or throat, but in fact no physical cooling such as in the evaporation of solvents takes place.
  • physiological cooling agents both individual components and mixtures can be used. It should be noted that not all compounds that affect in vitro receptors that (also) are involved in mediating a physiological cooling effect actually produce such an in vivo effect on the skin or on mucous membranes. In particular, such an effect will not always be identical. This means, for example, that the strength of the mediated physiological cooling effect and the course of the strength of the cooling effect over time can not be concluded solely from the fact that a particular compound is an argonist of a receptor involved in mediating a cooling impression.
  • the best known physiologically effective cooling agent is L-menthol, but has some disadvantages, for. B. strong odor impression, high volatility and in higher concentrations a bitter and / or pungent taste, or a skin irritant effect.
  • a ⁇ (menthane carbonyl) alkyloxyalkylamides have been described in JP 2004059474. However, they have the disadvantage of being very bitter with strong cooling effect and high hydrolytic stability, and they are therefore not applicable in food and also in facial care cosmetic products.
  • cooling substances menthyl glyoxylates and their hydrates have been described in JP 2005343795 as cooling substances.
  • coolants produced and used heretofore, see M. Erman, Perfumer & Flavorist 32 (10), 20-35 (2007) and ML Dewis in DJ Rowe, Chemistry and Technology of Flavors and Fragrances, Blackwell Publishing Ltd, Oxford 2005 , p. 212-222.
  • Cooling substances can be used.
  • the compounds or mixtures of compounds to be indicated should preferably have the lowest possible intrinsic taste, in particular taste little or no bitter and should not be irritating as much as possible.
  • agents with active ingredients which can mediate a particularly long-lasting cooling sensation.
  • these agents should preferably be able to impart particularly intensive and / or rapid onset cooling impressions.
  • the compounds to be used according to the invention are contained in the agent to be investigated in a concentration of more than 100 ppm, it is preferred that the agent to be tested is used to evaluate whether the cooling effect is prolonged compared to WS3 to dilute that the compounds according to the invention (from Table 0) are present in a concentration of 100 ppm.
  • the same dilution step should also be carried out for the comparator containing WS3.
  • the cooling effect of the agents with the compounds to be used according to the invention is extended by at least 15 minutes, more preferably at least 20 minutes and particularly preferably at least 30 minutes, compared to the comparative experiments
  • the perceived cooling intensity on a scale of 0-9 to> 1, preferably> 2, more preferably> 3 and more preferably> 4 compared to an agent of the same composition in which only the compound to be used according to the invention Menthan-3-carboxylic acid N-ethylamide was replaced in the same concentration is increased.
  • the perceived intensity on the same scale is correspondingly increased after 20 minutes by> 1, preferably> 2, more preferably> 3 and very particularly preferably greater than or equal to 4.
  • the perceived intensity under the conditions described above is increased by> 1, more preferably by> 2, after 30 minutes, and / or the perceived intensity or the above-described conditions is increased after 45 minutes to> 1, preferably> 2 is.
  • test Example 2 the comparative experiments with regard to the prolongation of the cooling effect to the comparison substance WS3 are to be carried out analogously to Test Example 2 in the case of doubt, whereby it is preferred that at concentrations in the compounds to be used according to the invention (compounds of Table 0) be> 100 ppm a dilution step takes place on the entire agent, so that these compounds are contained only in a concentration of 100 ppm in the agent to be tested, and wherein the dilution step is carried out analogously in the comparison agent (the agent containing WS3).
  • the test panel (cf. test example (2)) comprises at least 6 persons and the intensity impression values are averaged mathematically.
  • the compounds to be used according to the invention for the specific aspect of the invention may optionally be used as mixtures of isomers, racemates or pure enantiomers.
  • the compounds to be used according to the invention are synthetically accessible in a manner known per se. A number of manufacturing examples can be found later in this text. Surprisingly, the compounds to be used according to the invention (the compounds of Table 0) hardly show any other trigeminal effects such as acuity, tingling or anesthesia and are not bitter. At the same time, the compounds according to the invention within the scope of the customary formulations and preparation conditions in the range of pH 1 to pH 12, in particular in the range of pH 4 to pH 9, based on aqueous preparations, are resistant to hydrolysis, so that the compounds of the invention and mixtures in preparations long are durable, so that the preparation itself is durable for a long time.
  • the invention also relates to an agent selected from the group consisting of aroma mixture and the nutrition, oral hygiene or pleasure pharmaceutical or cosmetic preparation comprising two, three or more of the compounds selected from group B consisting of
  • the invention preferably relates to an i) above-described agent according to the invention and / or ii) agent selected from the group consisting of flavoring mixture and nutrition, oral hygiene or pleasure pharmaceutical or cosmetic preparation, comprising one selected from two, three or more of the compounds consisting of the group C consisting
  • Peppermint oil 0.30 g
  • nonionic surfactant 5.00 g
  • the compounds to be used according to the invention are preferred in a (total) concentration of from 0.05 ppm to 50% by weight, based on the total weight of the preparation or of the composition contain.
  • this range is composed of the following sub-ranges: 0.05 ppm - ⁇ 0.1 ppm. 0, 1 ppm - 1,000 ppm and 0, 1 - 50 wt .-%.
  • Preferred concentration ranges, based on the total weight of the preparation or of the agent are the following, the concentration ranges in the enumerated sequence being more preferred in each case than in the previous enumeration member:
  • compositions especially those in the preferred variant are able to provide a long-lasting cooling effect on the skin or mucosa, without the invention used according to compounds (the compounds of Table 0) the intended use of the respective Prevent or restrict by means.
  • Such a composition more preferably comprises one or more further substances having a physiological cooling effect without a taste effect. This avoids that with the agent according to the invention, for example, only flavors with a minty aroma character can be obtained.
  • an agent according to the invention comprising as component (2) one or more flavoring substances without physiological cooling effect and / or as constituent (3) one or more compounds which independently or together additionally have a taste-modulating effect and / or a triglycemic and / or cause a mouth-watering stimulus, wherein the trigiminal stimulus preferably does not represent a physiological cooling effect.
  • agents according to the invention which contain the latter components (2) and (3) at the same time, have a pleasant cooling effect and a balanced sensory profile with simultaneously high impact, i. high taste first impression.
  • the special aspect of the invention preferably also relates to agents, in particular as nutrition, oral hygiene or pleasure or pharmaceutical or cosmetic preparations, which have a sufficient amount to achieve a physiological cooling effect on the skin and / or mucous membrane of a compound to be used according to the invention from Table 0) or a mixture of such compounds to be used according to the invention.
  • agents in particular as nutrition, oral hygiene or pleasure or pharmaceutical or cosmetic preparations, which have a sufficient amount to achieve a physiological cooling effect on the skin and / or mucous membrane of a compound to be used according to the invention from Table 0) or a mixture of such compounds to be used according to the invention.
  • the amount of this compound or mixture used to achieve a physiological cooling effect on the mucosa in the mouth, nose and / or throat should be sufficient.
  • a preparation must be prepared by means of a working step which goes beyond simply mixing the individual compounds. Such an operation may serve, for example, to produce a suspension or emulsification.
  • Preferred agents according to the invention comprise conventional basic substances, adjuvants and additives for nutrition, oral hygiene or for pleasure or pharmaceutical or cosmetic preparations.
  • Preferred preparations according to the invention comprise 0.000005% by weight to 20% by weight, preferably 0.00001 to 10% by weight, particularly preferably 0.0001% by weight to 0.5% by weight, of compounds to be used according to the invention Table 0, based on the Total weight of the preparation.
  • constituents (1) other substances having a physiological cooling effect
  • constituents (2) flavoring substances without physiological cooling effect
  • / or (3) trigeminal or watering substances having no physiological cooling effect
  • Auxiliaries and additives may be present in amounts of 0.0000001 to 99.99% by weight, preferably 10 to 80% by weight, based on the total weight of the preparation.
  • the preparations according to the invention may contain water in an amount of up to 99.99% by weight, preferably 5 to 80% by weight, based on the total weight of the preparation.
  • an agent according to the invention wherein at least one of the compounds selected from the group A is selected from the group consisting of D
  • agent according to the invention wherein at least one of the compounds selected from the group A is selected from the group E, consisting of
  • the compounds of Table 0 and / or their mixtures to be used according to the invention are preferably used for the preparation of a medicament for combating or alleviating cough, cold, mouth, nose, throat or pharyngeal, sore throat or hoarseness symptoms ,
  • Another aspect of the specific aspect of the present invention relates to a therapeutic or non-therapeutic method for achieving a physiological cooling effect on the skin and / or a mucous membrane, with the following step:
  • the agent according to the invention being an aroma mixture which comprises one or more flavoring substances and / or one or more further cooling active substances (cooling agents which are not compounds of Table 0) for flavoring manufactured goods using the aroma mixture.
  • the content of the substances to be used according to the invention of Table 0 is from 0.001 to 50% by weight; preferred is a range of 0.005 to 5 wt .-% and particularly preferably a range of 0.01 to 2 wt .-%.
  • the content of the present invention to be used substances of formula I is 0.000005 to 0.75% by weight based on the finished product; Accordingly, a range of 0.000025 to 0.075 wt .-% and particularly preferably corresponding to a content of 0.00005 to 0.03 wt .-% is preferred.
  • the content of the substances to be used according to the invention of Table 0 is 0.005 to 10% by weight; preferred is a range of 0.01 to 5 wt .-% and particularly preferably a range of 0.05 to 2.5 wt .-%.
  • the content of the substances of Table 0 to be used according to the invention is 0.00005 to 0.2% by weight, based on the finished product; Accordingly, a range of 0.0001 to 0.1 wt .-% and particularly preferably according to a content of 0.0005 to 0.05 wt .-% is preferred.
  • the content of the substances to be used according to the invention of Table 0 is from 0.01 to 10% by weight; preferred is a range of 0.05 to 5 wt .-% and particularly preferably a range of 0, 1 to 2.5 wt .-%.
  • a typical dosage of the aroma of 2 to 4 wt .-% based on a ready-to-use mouthwash concentrate then the content of the present invention to be used substances of Table 0 0.0002 to 0.4 wt% based on the finished product; Accordingly, a range of 0.001 to 0.2% by weight and particularly preferably a content of 0.002 to 0.1% by weight is correspondingly preferred.
  • finished mouthwashes and rinses is then at a conventional dosage of the aroma mixture of 0.1 to 0.3 wt .-% of the content of the present invention to be used in Table 0 0.00001 to 0.03% by weight based on the finished product; Accordingly, a range of 0.00005 to 0.015 wt .-% and particularly preferably corresponding to a content of 0.0001 to 0.0075 wt .-% is preferred.
  • Suitable flavoring agents are both complex natural raw materials such as extracts and essential oils derived from plants, or fractions and uniform substances obtained therefrom, as well as uniform synthetic or biotechnologically derived flavorings.
  • Examples of natural raw materials are, for example:
  • uniform flavorings are, for example:
  • the content of the substances of Table 0 to be used according to the invention is from 0.000005 to 0.1% by weight; preferred is a range of 0.00005 to 0.05 wt .-%, and more preferably a range of 0.0001 to 0.02 wt .-%.
  • the content of the substances to be used according to the invention of Table 0 is from 0.001 to 10% by weight; preferred is a range of 0.005 to 5 wt .-% and particularly preferably a range of 0.01 to 2 wt .-%. It is particularly preferred according to the invention for the agent according to the invention to be a toothpaste in accordance with the specific aspect of the invention.
  • Component in particular of the specific aspect of the invention is also a compound selected from the group consisting of
  • the active substances of the structure types 1, 2 and 3 used according to the invention are either compounds known per se or can be prepared on the basis of known synthesis methods by a person skilled in the art of organic synthesis.
  • the starting point for the cloning of the human TRPM8 receptor is an LnCaP cDNA library.
  • LnCaP cDNA library This is, for example, commercially available (e.g., BioChain, Hayward, U.S.A.) or from the androgen-sensitive human prostate adenocarcinoma cell line LnCaP (e.g., ATCC, CRL1740, or ECACC, 891 1021 1) using standard kits.
  • the coding TRPM8 sequence (cf., FIG. 1)
  • TRPM8 gene can also be produced synthetically.
  • HEK293 As a test cell system stably transfected HEK293 cell line was prepared with the human TRPM8 DNA (see above plasmid plnd-M8). HEK293 is preferred here, which offers the possibility of inducing TRPM8 expression by means of tetracycline via the introduced plasmid.
  • the agonization or antagonization of the receptor can be quantified by means of a Ca 2+ -sensitive dye (eg FURA, Fluo-4, etc.).
  • a Ca 2+ -sensitive dye eg FURA, Fluo-4, etc.
  • Agonists alone cause an increase in the Ca 2+ signal;
  • antagonists bring about a reduction in the Ca 2+ signal (detected in each case via the dye fluo-4, which has other fluorescence properties due to Ca 2+ ).
  • a fresh culture of transformed HEK cells is prepared in a conventional manner in cell culture bottles.
  • the test cells HEK293-TRPM8 are detached from the cell culture bottles by means of trypsin and 40,000 cells / well are seeded with 100 ⁇ M medium in 96-well plates (Greiner # 655948 poly-D-lysine coated).
  • the receptor TRPM8 tetracycline is added to the growth medium (DMEM / HG, 10% FCS tetracycline free, 4 mM L-glutamine, 15 ug / ml blasticidin, 100 ug / ml hygromycin B, 1 ug / ml tetracycline).
  • the cells are loaded with Fluo-4AM dye and the test is performed.
  • the procedure is as follows:
  • test substances different concentrations in 200 ⁇ HBSS buffer
  • positive controls different concentrations of menthol, icilin or ionomycin in 200 ⁇ HBSS buffer
  • negative controls only 200 ⁇ HBSS buffer
  • test substances are used in triplicates in concentrations of 0.1-200 ⁇ in the assay. Normally, the compounds are stored in DMSO solutions and diluted down to a maximum DMSO concentration of 2% for the assay.
  • the compounds of the formula I are obtainable from the reaction of keto precursors of the formula VI with the ketoreactive compound of the formula Yl (see Akhrem et al., Kimiya Geteotsiklicheskikh Soedinenii, 1995, 187-194, Akhrem et al., Journal of Organic Chemistry of the USSR, 1985, 21 (6), 1227-1232)
  • the suspension is filtered and the filter cake washed with 15 ml of toluene. After drying for 2 h in a vacuum drying oven at 50 ° C., 12.4 g of solid are isolated. The solid is dissolved in 15 ml of toluene and filtered hot through a sand / diatomaceous earth / activated carbon filter. The filter is rinsed with 15 ml of hot toluene. 80 ml of toluene are distilled off and the concentrated reaction mixture is cooled to -10 ° C. The suspension is filtered and the filter cake washed with a little cold toluene. It is dried overnight in a vacuum oven at 50 ° C to give compound 1 -1
  • the precipitated solid is filtered off, washed with ethyl acetate and dried in vacuo at 50 ° C.
  • the solid is mixed with 100 ml of isopropanol and 70 ml of isopropanol are distilled off again via a Vigreux column.
  • the suspension is cooled to 0 ° C.
  • the solid is filtered off, washed with a little cold isopropanol and dried to give the desired compound. Yield: 6.9 g (67%)
  • a mixture of 1, 6 g (7.8 mmol) of 2-E and 1 1, 04 g (187 mmol) of isopropylamine are stirred for 42 h at room temperature.
  • the batch is concentrated by rotary evaporation and treated with water, 1.33 eq NaOH and dichloromethane.
  • the aqueous phase is separated and extracted once more with dichloromethane.
  • the combined organic phases are dried over sodium sulfate, filtered and concentrated by rotary evaporation.
  • the residue is stirred with hot MTBE and the suspension is then cooled to room temperature. It is filtered, the residue with little MTBE gewa- see and dried at 50 ° C in a vacuum oven to obtain the desired compound.
  • the reaction is carried out, for example, in an apolar organic solvent in the presence of an acid scavenger.
  • the mixture is then stirred at 60-65 ° C for 16 h. It is hydrolyzed with water and the organic phase after phase separation once again washed at 60 ° C with water. It is filtered hot and evaporated. The residue is crystallized from isopropanol. The crystallized solid is filtered off with suction at 0 ° C., washed with iPrOH and dried to give the desired compound.
  • the mixture is stirred for 30 min at 60 ° C and cooled to RT.
  • the reaction mixture is treated with water and 2-methyltetrahydrofuran and heated to 70 ° C.
  • the organic phase is washed twice with water, once with 1N sodium hydroxide solution and twice with water at 50.degree.
  • the organic phase is concentrated by rotary evaporation and recrystallised from n-heptane.
  • the crystallized solid is filtered off with suction at 0 ° C., washed with n-heptane and dried to give the desired compound.
  • a solution of 6.8 g (0.037 mol) of cyclohexyl-2-pyridylamine in toluene is metered in and stirred at 60 ° C. for 1 h. It is hydrolyzed with water and added 2-methyltetrahydrofuran. The organic phase is separated and washed with water, 1 N NaOH and again with water. The organic phase is concentrated by rotary evaporation and the residue is crystallized from MTBE. The crystallized solid is filtered off with suction, washed with MTBE and dried to give the desired compound.
  • a solution of 5.2 g (0.030 mol) of N-cyclohexyl-2-pyridylamine in toluene is metered in and stirred at 50 ° -60 ° C. for 1 hour. It is hydrolyzed with water at 50-60 ° C. The organic phase is separated and washed with water, 1 N NaOH and again with water. The organic phase is filtered, concentrated by rotary evaporation and the residue is crystallized from toluene. The crystallized solid is filtered off with suction at 0 ° C., washed with toluene and dried to give the desired compound.
  • Formulation Example FM-1 Mouthwash Suitable mouthwashes can be prepared according to the following basic recipe:
  • a mouthwash of the following composition is prepared:
  • Suitable toothpastes can be prepared according to the following basic formulation:
  • Suitable chewing gums can be prepared according to the following basic formulation:
  • sugar alcohols mannitol, xylitol and sorbitol, "palatinit” and others as well as artificial sweeteners such as saccharin, cyclamate, acesulfame-K and aspartame can also be used for "sugar-free" formulations.
  • Preparation Mix phase A. Add phase B and stir until everything is dissolved, adjust pH to pH 7.0.
  • Preparation Weigh in the components of phase A and homogenize. Dissolve phase B and stir in phase A. Adjust pH to pH 6.9.
  • the following formulations describe a cosmetic sunscreen formulation containing a combination of at least one inorganic pigment and organic UV filters.
  • Formulation example FK-5 care shampoo
  • Preparation Mix and dissolve the components of phase A. Adjust the pH to 6-7 with citric acid.
  • Formulation example FK-7 shampoo
  • Preparation Heat the components of phases A and B separately from each other to approx. 80 ° C. Stir phase B into phase A while homogenizing. Cool with stirring to about 40 ° C, add the phases C and D and briefly nachhomogen gives. Cool to room temperature while stirring.
  • Formulation example FK-9 Facial cleansing lotion
  • Preparation Mix the components of phase A. Dissolve phase B, work in phase A and homogenize.
  • Preparation Heat the components of phases A and B separately from each other to approx. 80 ° C. Stir phase B into phase A and homogenize. Heat phase C to approx. 80 ° C and stir into the combined phases A and B while homogenizing. Cool with stirring to about 40 ° C, add phase D and homogenize again.
  • an aqueous slurry of amylose-containing starch is prepared by adding 570 grams of deionized water with 10 grams of a commercial preservative.
  • 20 g of carboxymethyl cellulose was dissolved, followed by the addition of 400 g of an amylose-containing starch having an amylose content of 50% by weight, and a slurry was prepared with stirring.
  • aqueous liquors containing amylose-containing starch are prepared by one of the following two methods:
  • Method 1 The respective slurry is adjusted to a starch content of 5 or 15% by weight by dilution with water.
  • Method 2 The respective slurry is first diluted with water to a starch content of 5 or 15 wt .-% and then treated with 30 g / l of a 30 wt .-%, aqueous polyurethane dispersion (non-ionic).
  • Cotton fabric sample having a basis weight of 124 g / m 2 is treated with one of the above-prepared liquors by means of a padder to a liquor pick-up of 80 wt .-%, based on the weight of the fabric. It is then dried for 2 min at 120 ° C.
  • the so-equipped tissue samples are treated with an aqueous active ingredient formulation by applying an aqueous emulsion / suspension of an active ingredient according to the invention with an active ingredient content of 1 to 7 wt .-% to a liquor uptake of 79 - 80 wt .-% on the fabric sample auffoulardiert. Subsequently, the thus treated fabric samples are dried in a household dryer to a residual moisture content of 15%.
  • the drug-loaded tissues thus prepared can then be further tested, e.g. on their cooling effect on skin contact or their repellent effect on insects.
  • the flavors thus obtained were incorporated into a standard toothpaste mass based on silica in a concentration of 1, 2 wt .-%.
  • the toothpastes were tested under practical conditions by a sensory expert panel.
  • the sensory evaluations showed: very beautiful, rich and voluminous minty freshness with a comparatively fast onset, strong and pronounced and comparatively very long-lasting cooling freshness impression, whereby it was striking that the feeling of cold could be perceived quickly throughout the mouth.
  • the aroma was judged to be softer and more neutral and less sharp than without the compounds of the invention.
  • the resulting flavors were incorporated at a concentration of 1.2% in a toothpaste mass consisting of 65% sodium bicarbonate.
  • the toothpastes were tested under practical conditions and evaluated by a sensory-trained expert panel. In each case, a beautiful, strong Krauseminzgeschmack was found in conjunction with a voluminous and long-lasting cooling freshness taste.
  • the flavors thus obtained were each incorporated into a standard toothpaste mass based on silica in a concentration of 1, 2 wt .-%.
  • the toothpastes were tested under practical conditions by a sensory-trained expert panel. The sensory evaluation showed in each case: very beautiful, minty, aromatic and spicy freshness with a very strong and pronounced, very long-lasting cooling freshness impression.
  • the flavors thus obtained were incorporated into a standard toothpaste mass based on silica in a concentration of 1, 2 wt .-%.
  • the toothpastes were tested under practical conditions by a sensory expert panel. The sensory evaluation showed in each case: pronounced fresh-minty wintergreen note, with a very strong and pronounced, very long-lasting cooling freshness impression.
  • the flavors thus obtained were each incorporated in a sugar-free standard chewing gum mass in a concentration of 1, 5 wt .-%.
  • the chewing gum was tested for sensory quality by a trained expert panel. It has been found that the flavors contain a pronounced freshness note by the addition of the substances according to the invention, which enhances the peppermint flavor and provides a long-lasting freshness sensation, which is still noticeable even after chewing the chewing gum for a long time.
  • the flavors thus obtained were each incorporated in a sugar-free standard chewing gum mass in a concentration of 1, 5 wt .-%.
  • the chewing gum was tested for sensory quality by a trained expert panel. It was found that the aromas obtained by the addition of the substances according to the invention a pronounced freshness note, which harmonizes very well with the typical Krauseminzgeschmack and provides a pronounced, long-lasting sense of freshness, even after chewing the chewing gum for a long time still clearly noticeable stops.
  • the flavors thus obtained were each incorporated in a sugar-free standard chewing gum mass in a concentration of 1, 5 wt .-%.
  • the chewing gums were prepared by a trained The expert panel was tested for its sensory quality. It was found that the aromas obtained by the addition of the cooling substances according to the invention a pronounced freshness note, which harmonizes well with the spicy-aromatic taste and provides a rapid onset throughout the oral cavity perceptible and long-lasting freshness sensation, which also after Chewing the chewing gum for a long time still noticeably persists. Overall, the aroma by the addition of cooling substances according to the invention is more harmonic and much less sharp.
  • the flavors were each incorporated at a concentration of 0.15% by weight in a ready-to-use mouthwash or at a concentration of 3% by weight in a mouthwash concentrate.
  • the sensory evaluation by a trained panel of experts showed that the aromas led to a fast onset, very long-lasting freshness effect, which continued even after use of the mouthwashes over a period of almost 1 h.
  • Toothpaste ('Silica opaque ')
  • Toothpaste (calcium carbonate base)
  • Toothpaste transparent gel formulation
  • Chewing gum (with sugar and sugar-free)
  • the preparation of the chewing gum base K1 and the chewing gums can be carried out analogously to US 5,601,858.
  • the preparation of the chewing gum base K2 and the chewing gum can be analogous to US 6,986,907 done.

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Abstract

L'invention concerne un modulateur du récepteur TRPM8 pour produire un effet de froid sur la peau ou les muqueuses.
PCT/EP2010/067936 2009-11-20 2010-11-22 Utilisation d'agents rafraîchissants physiologiques et produits contenant de tels agents WO2011061330A2 (fr)

Priority Applications (8)

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JP2012539353A JP6017310B2 (ja) 2009-11-20 2010-11-22 生理的冷感有効成分の使用およびそのような有効成分を含む薬剤
EP10787717.7A EP2501761B1 (fr) 2009-11-20 2010-11-22 Utilisation d'agents rafraîchissants physiologiques et produits contenant de tels agents
CN201911393855.4A CN111053775B (zh) 2009-11-20 2010-11-22 生理学清凉的活性成分以及含有这类活性成分的物质的用途
CN201080061894.5A CN102844386B (zh) 2009-11-20 2010-11-22 生理学清凉的活性成分以及含有这类活性成分的物质的用途
EP19194016.2A EP3663366A3 (fr) 2009-11-20 2010-11-22 Utilisation de substances actives de refroidissement physiologiques et moyen comportant des telles substances actives
ES10787717T ES2812550T3 (es) 2009-11-20 2010-11-22 Uso de principios activos refrescantes fisiológicos y agentes que contienen tales principios activos
US13/510,454 US8927605B2 (en) 2009-11-20 2010-11-22 Use of physiological cooling active ingredients, and agents containing such active ingredients
US15/629,015 US10584134B2 (en) 2009-11-20 2017-06-21 Use of physiological cooling active ingredients, and agents containing such active ingredients

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EP09176698 2009-11-20
EP09176698.0 2009-11-20
DE102010002558A DE102010002558A1 (de) 2009-11-20 2010-03-03 Verwendung physiologischer Kühlwirkstoffe und Mittel enthaltend solche Wirkstoffe
DE102010002558.5 2010-03-03

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US14/533,345 Division US9718839B2 (en) 2009-11-20 2014-11-05 Use of physiological cooling active ingredients, and agents containing such active ingredients

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JP2013511270A (ja) 2013-04-04
JP2017141220A (ja) 2017-08-17
CN102844386B (zh) 2020-01-21
CN102844386A (zh) 2012-12-26
WO2011061330A9 (fr) 2012-01-05
ES2812550T3 (es) 2021-03-17
DE102010002558A1 (de) 2011-06-01
US9718839B2 (en) 2017-08-01
JP2015180200A (ja) 2015-10-15
CN111053775B (zh) 2023-08-18
CN111053775A (zh) 2020-04-24
JP6096238B2 (ja) 2017-03-15
US20120263659A1 (en) 2012-10-18
US20150086491A1 (en) 2015-03-26
EP3663366A2 (fr) 2020-06-10
JP2015205871A (ja) 2015-11-19
EP2501761B1 (fr) 2020-06-17
US20180093997A1 (en) 2018-04-05
US8927605B2 (en) 2015-01-06
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EP3663366A3 (fr) 2020-07-22
EP2501761A2 (fr) 2012-09-26

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